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Here is a chemical reaction formula: Reactants are m6_m9:ClC(C(Cl)(Cl)Cl)(Cl)Cl, amount is: 0.0 ;m5_m8:C(C)N(C(C1=C(C=CC=C1)N(C(C)(C)C)C)=O)C, amount is: 0.0 ;m1_m2_m3_m4_m7:[Li]C(C)CC, amount is: 0.0 MOLE;m1_m2_m3_m4_m7:C1CCCCC1, amount is: 0.0 ;m1_m2_m3_m4_m7:C(=O)=O.CC(=O)C, amount is: 0.0 MOLE;m1_m2_m3_m4_m7:CN(C)CCN(C)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m6_m9:C1CCOC1, amount is: 0.0 ;m5_m8:C1CCOC1, amount is: 0.0 ;m1_m2_m3_m4_m7:C1CCOC1, amount is: 0.0 ;m10:O, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:ClC1=C(C(=O)N(C)CC)C(=CC=C1)N(C)C(C)(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 1.3M s-BuLi in cyclohexane (3.7 mL, 4.8 mmol) was added dropwise to a dry-ice/acetone cooled solution of TMEDA (0.7 mL, 4.8 mmol) in THF (10 mL), followed by the dropwise addition of a solution of N-ethyl-N-methyl 2-(N-methyl-N-tert-butylamino)benzamide (1.0 g, 4.0 mmol) in THF (5 mL). The reaction mixture was briefly warmed to -30° C., then cooled to -78° C. and stirred for 15 min. A solution of hexachloroethane (2.8 g, 12.1 mmol) in THF (5 mL) was added. This mixture was stirred for 1 h at -78° C., then was warmed to -30° C., diluted with water, and extracted with EtOAc (2×). The combined organic extracts were dried (MgSO4), concentrated, and purified by HPLC with 1:4 EtOAc/cyclohexane to give 528 mg of the title compound as a yellow oil, a 46% yield. |
Here is a chemical reaction formula: Reactants are m6_m9:ClC(C(Cl)(Cl)Cl)(Cl)Cl, amount is: 0.0 ;m1_m2_m3_m4_m7:[Li]C(C)CC, amount is: 0.0 MOLE;m1_m2_m3_m4_m7:C1CCCCC1, amount is: 0.0 ;m1_m2_m3_m4_m7:C(=O)=O.CC(=O)C, amount is: 0.0 MOLE;m1_m2_m3_m4_m7:CN(C)CCN(C)C, amount is: 0.0 ;m5_m8:CC(C)(C)N(C1=C(C(=O)NCC)C=CC=C1)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m6_m9:C1CCOC1, amount is: 0.0 ;m1_m2_m3_m4_m7:C1CCOC1, amount is: 0.0 ;m10:O, amount is: 0.0 MOLE;m5_m8:C1CCOC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC1=C(C(=O)NCC)C(=CC=C1)N(C)C(C)(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 1.3M s-BuLi in cyclohexane (5.7 mL, 7.5 mmol) was added dropwise to a dry-ice/acetone cooled solution of TMEDA (0.5 mL, 3.6 mmol) in THF (10 mL), followed by the dropwise addition of a solution of the compound of Example 188 (0.7 g, 3.0 mmol) in THF (5 mL). The reaction mixture was stirred at -78° C. for 30 min, then hexachloroethane (2.1 g, 9.0 mmol) in THF (5 mL) was added. This mixture was stirred for 30 min at -78° C., then was warmed to -30° C., diluted with water, and extracted with EtOAc (2×). The combined organic extracts were dried (MgSO4), concentrated, and purified by HPLC with 3:17 EtOAc/cyclohexane to give 495 mg of the title compound as a yellow solid, an 61% yield. m.p. 106°-108° C. |
Here is a chemical reaction formula: Reactants are m5_m8:CC(C)(C)N(C1=C(C(=O)NCC)C=CC=C1)C, amount is: 0.0 ;m1_m2_m3_m4_m7:[Li]C(C)CC, amount is: 0.0 MOLE;m1_m2_m3_m4_m7:C1CCCCC1, amount is: 0.0 ;m1_m2_m3_m4_m7:C(=O)=O.CC(=O)C, amount is: 0.0 MOLE;m1_m2_m3_m4_m7:CN(C)CCN(C)C, amount is: 0.0 ;m6:CI, amount is: 0.0 ,this reaction does not need reagents,Solvents are m5_m8:C1CCOC1, amount is: 0.0 ;m9:O, amount is: 0.0 MOLE;m1_m2_m3_m4_m7:C1CCOC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C)NC(C1=C(C=CC=C1C)N(C)C(C)(C)C)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 1.3M s-BuLi in cyclohexane (9.8 mL, 12.8 mmol) was added dropwise to a dry-ice/acetone cooled solution of TMEDA (0.6 mL, 3.8 mmol) in THF (10 mL), followed by the dropwise addition of a solution of the compound of Example 188 (0.75 g, 3.2 mmol) in THF (5 mL). The reaction mixture was stirred at -78° C. for 30 min, then methyl iodide (2.3 g, 16 mmol) was introduced in a single portion. This mixture was stirred for 2.5 h at -78° C., then was warmed to -30° C., diluted with water, and extracted with EtOAc (2×). The combined organic extracts were dried (MgSO4), concentrated, and purified by HPLC with 1:4 EtOAc/cyclohexane to give 146 mg of the title compound as a light yellow solid, an 18% yield. m.p. 101°-103° C. |
Here is a chemical reaction formula: Reactants are m1_m4:C(C)NC(C1=C(C=CC=C1SC(C)(C)C)F)=O, amount is: 0.0 ;m2:OOS(=O)[O-].[K+], amount is: 0.0 MOLE;m3:S(=O)(=O)([O-])S(=O)[O-].[Na+].[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4:CO, amount is: 0.0 ;m5:O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:CC(C)(C)S(=O)C1=C(C(=O)NCC)C(=CC=C1)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A 0° C. solution of N-ethyl-2-fluoro-6-(1,1-dimethylethylthio)benzamide (3.45 g, 13.51 mmol) in methanol (100 mL) was combined with a 0° C. solution of OXONE® (8.31 g, 13.51 mmol) in water (100 mL). This mixture was stirred for 2 min, then was poured into 25% aq sodium metabisulfite (100 mL) and extracted with ether (3×100 mL). The combined organics were washed with brine followed with water, then was dried (MgSO4), concentrated, and recrystallized from ethyl acetate--hexanes to afford 2.2 g of the title compound as a white solid, a 60% yield. m.p. 114°-116° C. |
Here is a chemical reaction formula: Reactants are m2:OOS(=O)[O-].[K+], amount is: 0.0 MOLE;m3:S(=O)(=O)([O-])S(=O)[O-].[Na+].[Na+], amount is: 0.0 ;m1_m4:ClCCNC(C1=C(C=CC=C1SC(C)(C)C)F)=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m5:O, amount is: 0.0 ;m1_m4:CO, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClCCNC(C1=C(C=CC=C1F)S(=O)C(C)(C)C)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A 0° C. solution of N-(2-chloroethyl)-2-fluoro-6-(1,1-dimethylethylthio)benzamide (2.0 g, 7.0 mmol) in methanol (50 mL) was combined with a 0° C. solution of OXONE® (4.24 g, 7.0 mmol) in water (50 mL). This mixture was stirred for 2 min, then was poured into 25% aq sodium metabisulfite (100 mL) and extracted with ether (3×100 mL). The combined organics were washed with brine followed with water, then were dried (MgSO4), concentrated, and purified by HPLC with 7:3 ethyl acetate/hexanes to afford 2.1 g of the title compound as a white solid, a 98% yield. m.p. 80°-90° C. |
Here is a chemical reaction formula: Reactants are m2:C(C)N, amount is: 130.0 MILLIMOLE;m1:ClC1=C(C(=O)Cl)C=C(C=C1)Cl, amount is: 51.0 MILLIMOLE,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:C(C)NC(C1=C(C=CC(=C1)Cl)Cl)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 2,5-Dichlorobenzoyl chloride (51 mmol) and 70% aq EtNH2 (130 mmol) were combined according to General Method E1 to afford 9.4 g of N-ethyl-2,5-dichlorobenzamide as a beige solid, an 85% yield. |
Here is a chemical reaction formula: Reactants are m1_m6_m2_m3_m4_m5:[Li+].CC(C)[N-]C(C)C, amount is: 0.0 MOLE;m1_m6_m2_m3_m4_m5:CCOCC, amount is: 0.0 MOLE;m1_m6_m2_m3_m4_m5:C(C)NC(C1=C(C=CC(=C1)Cl)Cl)=O, amount is: 0.0 ;m1_m6_m2_m3_m4_m5:C[Si](C)(C)Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m6_m2_m3_m4_m5:C1CCOC1, amount is: 0.0 ;m1_m6_m2_m3_m4_m5:C1CCOC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC=1C(=C(C(=O)NCC)C(=CC1)Cl)[Si](C)(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 1.5M LDA in THF (13 mL, 19.5 mmol) was added dropwise to an ether/liquid N2 cooled solution of N-ethyl 2,5-dichlorobenzamide (2.0 g, 9.2 mmol) and TMSCl (1.5 mL, 11.5 mmol) in THF (50 mL), maintaining the internal reaction temperature ≤-80° C. The resulting reaction mixture was stirred at -100° C. for 30 min, then was partitioned between ether and sat aq NaHCO3. The ether solution was dried (MgSO4), concentrated, and crystallized from EtOAc/hexanes to afford 1.15 g of the title compound as a white solid. m.p. 150°-153° C. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4_m5_m7:[Li]C(C)CC, amount is: 0.0 MOLE;m1_m2_m3_m4_m5_m7:C1CCCCC1, amount is: 0.0 ;m1_m2_m3_m4_m5_m7:C(=O)=O.CC(=O)C, amount is: 0.0 MOLE;m1_m2_m3_m4_m5_m7:CN(C)CCN(C)C, amount is: 0.0 ;m1_m2_m3_m4_m5_m7:C(C)N(C(C1=C(C=CC=C1)Cl)=O)C(C(C)(C)C)OC, amount is: 0.0 ;m6:C[Si](C)(C)Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m4_m5_m7:C1CCOC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC1=C(C(=O)N(C(C(C)(C)C)OC)CC)C(=CC=C1)[Si](C)(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 1.3M s-BuLi in cyclohexane (3.53 mL, 4.59 mmol) was added to a dry ice/acetone cooled solution of TMEDA (639 mL, 4.23 mmol) and N-ethyl-N-(1-methoxy-2,2-dimethylpropyl)-2-chlorobenzamide (1.0 g, 3.53 mmol) in THF (7 mL). The resulting mixture was stirred at -78° C. for 45 min, then TMSCl (671 mL, 5.29 mmol) was added in a single portion. The reaction was allowed to warm to 0° C., and partitioned between ether and 10% HCl. The ether solution was then extracted with sat aq NaHCO3, dried (MgSO4), and purified by RC with 1:49 EtOAc/hexanes to afford 750 mg of the title compound as a white solid, a 60% yield. m.p. 82°-83° C. |
Here is a chemical reaction formula: Reactants are m1_m2:C(C)NC(C1=C(C=CC=C1[Si](C)(C)C)I)=O, amount is: 0.0 MOLE;m1_m2:C(C#C)N, amount is: 0.0 MOLE,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:IC1=C(C(=O)NCC#C)C(=CC=C1)[Si](C)(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The acid chloride prepared in Example 207 was reacted with propargylamine (3 eq) using General Method E1 to afford the title compound. Purification by recrystallization from hexanes gave 0.48 g of the title compound as an off-white solid in 85% yield. m.p. 109°-111° C. |
Here is a chemical reaction formula: Reactants are m1_m2:C(C)NC(C1=C(C=CC=C1[Si](C)(C)C)I)=O, amount is: 0.0 MOLE;m1_m2:C1(CC1)N, amount is: 0.0 MOLE,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:C1(CC1)NC(C1=C(C=CC=C1[Si](C)(C)C)I)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The acid chloride prepared in Example 207 was reacted with cyclopropylamine (3 eq) using General Method E1 to afford the title compound. Purification by recrystallization from hexanes gave 0.49 g of the title compound as white needles in 87% yield. m.p. 162°-164° C. |
Here is a chemical reaction formula: Reactants are m4:C(OC(C)(C)C)(OC(C)(C)C)=O, amount is: 0.0 ;m1_m2_m5_m6:ClC1=C(C(=O)NCC)C(=CC=C1)[Si](C)(C)C, amount is: 0.0 ;m1_m2_m5_m6:C(OC(C)(C)C)(OC(C)(C)C)=O, amount is: 0.0 ;m1_m2_m5_m6:C(C)#N, amount is: 0.0 MOLE;m3:C(OC(C)(C)C)(OC(C)(C)C)=O, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,Catalysts are m1_m2_m5_m6:CN(C1=CC=NC=C1)C, amount is: 0.0 .Products are 0:ClC1=C(C(=O)CCNC(OC(C)(C)C)=O)C(=CC=C1)[Si](C)(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of the compound of example 45 (3.83 g, 15 mmol) and di-t-butyl carbonate (3.60 g, 16.5 mmol) in acetonitrile was added 4-dimethylaminopyridine (0.18 g, 1.5 mmol). The solution was stirred at RT for 1 day, additional di-t-butyl carbonate (3.60 g) was added and stirring was continued for 3 days. Additional di-t-butyl carbonate (3.60 g) was added and the reaction was stirred overnight and concentrated. The residue was diluted with ether, washed with sat citric acid, sat NaHCO3, brine, dried (MgSO4) and concentrated to afford the title compound. The crude product was purified by flash chromatography (ethyl acetate /hexanes) and recrystallization from hexanes (-78° C.) to afford the title compound as a white solid (2.65 g, 50%). m.p. 51°-52° C. |
Here is a chemical reaction formula: Reactants are m1_m2_m6_m3_m4:ClC1=C(C(=O)N(C(C(C)(C)C)OC)CC)C(=CC=C1)[Si](C)(C)C, amount is: 0.0 ;m1_m2_m6_m3_m4:CN(C)CCN(C)C, amount is: 0.0 ;m1_m2_m6_m3_m4:[Li]C(C)CC, amount is: 0.0 MOLE;m1_m2_m6_m3_m4:C1CCCCC1, amount is: 0.0 ;m5:BrCCBr, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m6_m3_m4:C1CCOC1, amount is: 0.0 ;m7_m8:CC(=O)C, amount is: 0.0 ;m7_m8:Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:BrC=1C(=C(C(=O)NCC)C(=CC1)[Si](C)(C)C)Cl, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of the compound of Example 201 (0.79 g, 2.2 mmol) and TMEDA (0.44 mL, 2.9 mmol) in THF (20 mL) at -78° C. was added a solution of 0.86M s-BuLi in cyclohexane (3.3 mL, 2.9 mmol). The reaction was stirred at -78° C. for 30 min and 1,2-dibromoethane (0.26 mL, 3.0 mmol) was added. The reaction was stirred for 15 min at -78° C. and was quenched with sat NaHCO3. The mixture was extracted with ether, washed with brine, dried (MgSO4) and concentrated to afford a yellow oil. This oil was dissolved in a mixture of acetone (30 mL) and 6N HCl (15 mL) and was stirred overnight. The mixture was concentrated, extracted with ether, the organic layers washed with brine, dried (MgSO4) and concentrated to afford the title compound as a clear oil. The crude product was purified by RC (ethyl acetate/hexanes) and was recrystallized from pentane (-78° C.) to afford 76 mg of a white solid (10% yield). m.p. 105°-106° C. |
Here is a chemical reaction formula: Reactants are m1_m2_m6:C(C)NC(C1=C(C=CC=C1)C1=CC=CC=C1)=O, amount is: 0.0 ;m1_m2_m6:CN(C)CCN(C)C, amount is: 0.0 MOLE;m3_m4:[Li]C(C)CC, amount is: 0.0 MOLE;m3_m4:C1CCCCC1, amount is: 0.0 MOLE;m5:C[Si](C)(C)Cl, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m2_m6:C1CCOC1, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:C(C)NC(C1=C(C=CC=C1[Si](C)(C)C)C1=CC=CC=C1)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: This amide (2.25 g, 10 mmol) and TMEDA (1.2 eq) in THF were mixed and cooled to -78° C. and a 1.3M s-BuLi solution in cyclohexane (2.2 eq) was added dropwise. The resulting reaction mixture was stirred at -78° C. for 30 min and TMSCl (1.2 eq) was added dropwise. The reaction was stirred at -78° C. for 30 min and allowed to warm to -30° C. The reaction was worked up in the usual manner. The crude product was purified by flash chromatography and recrystallization from hexanes to afford the title compound as a white solid (1.15 g, 39%). m.p. 159°-160° C. |
Here is a chemical reaction formula: Reactants are m5:BrCCBr, amount is: 0.0 ;m1_m2_m6_m3_m4:ClC1=C(C(=O)N(C(C(C)(C)C)OC)CC)C(=CC=C1)[Si](C)(C)C, amount is: 0.0 ;m1_m2_m6_m3_m4:CN(C)CCN(C)C, amount is: 0.0 ;m1_m2_m6_m3_m4:[Li]C(C)(C)C, amount is: 0.0 MOLE;m1_m2_m6_m3_m4:CCCCC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m7:C(=O)(O)[O-].[Na+], amount is: 0.0 MOLE;m1_m2_m6_m3_m4:C1CCOC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:CN(C=1C=CC(=C(C(=O)N(C(C(C)(C)C)OC)CC)C1)[Si](C)(C)C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of the compound of Example 201 (0.72 g, 2.0 mmol) and TMEDA (1.20 mL, 8.0 mmol) in THF (30 mL) at -78° C. was treated with a solution of 1.7M t-BuLi in pentane (5.6 mL, 9.6 mmol) and allowed to slowly warm to -20° C. over 4 h. The reaction was quenched with 1,2-dibromoethane (0.86 mL, 10 mmol), was diluted with sat NaHCO3, extracted with ether, the organic layers washed with brine, dried (MgSO4) and concentrated to afford the title compound. The crude product was purified by RC (ethyl acetate/hexanes) and recrystallization from pentane (-78° C.) to afford the title compound as a white solid (0.14 g, 20%). m.p. 96°-98° C. |
Here is a chemical reaction formula: Reactants are m2:I[Si](C)(C)C, amount is: 0.0 ;m1_m3:CN(C=1C=CC(=C(C(=O)N(C(C(C)(C)C)OC)CC)C1)[Si](C)(C)C)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3:ClCl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:CN(C=1C=CC(=C(C(=O)NCC)C1)[Si](C)(C)C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The compound of Example 222 (0.31 g, 0.85 mmol) was dissolved in CH2 Cl2 (20 mL) and was treated with iodotrimethylsilane (2.1 mL, 15 mmol) in a foil-covered flask. The reaction was stirred for 2 h and was quenched with sat NaHCO3. The mixture was extracted with ether, the organic layers were washed with brine and sat sodium bisulf ite, dried (MgSO4) and concentrated to afford the title compound. The crude product was purified by RC (ethyl acetate/hexanes) and recrystallized from hexanes to afford 68 mg (5%) of the title compound as a white solid. m.p. 141°-143° C. |
Here is a chemical reaction formula: Reactants are m3:C(C)(=O)OC(C)=O, amount is: 0.0 ;m1_m2_m4:ClC1=C(C(=O)NCC)C(=CC=C1C=O)[Si](C)(C)C, amount is: 0.0 ;m1_m2_m4:Cl.NO, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m4:N1=CC=CC=C1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC1=C(C(=O)NCC)C(=CC=C1C#N)[Si](C)(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of the compound of Example 223 (0.28 g, 1.0 mmol) and hydroxylamine hydrochloride (0.12 g, 1.7 mmol) in pyridine (10 mL) was stirred at RT for 2 h. Acetic anhydride (0.75 mL, 8.0 mmol) was added and the solution was heated at 100° C. for 1.5 h. The mixture was concentrated, water added and the mixture extracted with ether. The organic layers were washed with 0.5 N HCl, sat NaHCO3, brine, dried (MgSo4) and concentrated to afford the title compound. The crude product was purified by recrystallization from ethyl acetate/hexanes to afford 0.21 g of white needles (74%). m.p. 111°-112° C. |
Here is a chemical reaction formula: Reactants are m0_m1_m2:C(C)(C)(C)C1=CC=C(C(=O)Cl)C=C1, amount is: 0.0 ;m0_m1_m2:C(C)N, amount is: 0.0 MOLE,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:C(C)(C)(C)C1=CC=C(C(=O)NCC)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 4-t-Butyl-N-ethylbenzamide (9 g, 0.044 mol) was prepared in 97% yield from 4-t-butylbenzoyl chloride (9 ml, 0.045 mol) and ethyl amine (70 wt % in water) using Method E2. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4_m7:[Li]C(C)CC, amount is: 0.0 MOLE;m1_m2_m3_m4_m7:C1CCCCC1, amount is: 0.0 ;m1_m2_m3_m4_m7:C(C)(C)(C)C1=CC=C(C(=O)NCC)C=C1, amount is: 0.0 ;m1_m2_m3_m4_m7:CN(C)CCN(C)C, amount is: 0.0 ;m6:C(=O)(O)[O-].[Na+], amount is: 0.0 MOLE;m5_m8:ClC(C(Cl)(Cl)Cl)(Cl)Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m4_m7:C1CCOC1, amount is: 0.0 MOLE;m5_m8:C1CCOC1, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:ClC1=C(C(=O)NCC)C=CC(=C1)C(C)(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 1.3M s-BuLi in cyclohexane (41 mL, 0.053 mol) was added dropwise to a solution of the above amide (5 g, 0.024 mol) and TMEDA (4 ml, 0.027 mol) in THF, cooled to -78° C. under nitrogen. After 30 min a solution of hexachloroethane (6.4 g, 0.027 mol) in THF was added. After 0.5 h at -78° C. the reaction mixture was warmed to -30° C. and poured into dilute aq NaHCO3 and extracted with ether. The ether extract was washed with water and brine, dried (MgSO4) and concentrated. The resulting solid was recrystallized from cyclohexane to give 5 g of 2-chloro-4-t-butyl-N-ethylbenzamide, a white solid. |
Here is a chemical reaction formula: Reactants are m4:O, amount is: 0.0 MOLE;m1_m2_m3_m5:ClC1=C(C(=O)NCC)C=C(C=C1)N, amount is: 0.0 ;m1_m2_m3_m5:C([O-])([O-])=O.[K+].[K+], amount is: 0.0 ;m1_m2_m3_m5:CI, amount is: 0.0 ;m1_m2_m3_m5:CN(C)C=O, amount is: 0.0 MOLE,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:C(C)NC(C1=C(C=CC(=C1)N(C)C)Cl)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of the above amine (3 g, 0.015 mol), potassium carbonate (3.8 g, 0.028 mol) and MeI (1.4 mL, 0.022 mol) in DMF stirred at RT overnight. The reaction mixture was poured into water and extracted with ether. The ether layer was washed with water and brine, dried (MgSO4) and concentrated to give an oil. Purification by flash chromatography (0-50% ethyl acetate/ hexanes) gave N-ethyl 2-chloro-5-(dimethylamino)benzamide as a yellow solid in 29% yield. |
Here is a chemical reaction formula: Reactants are m1_m4_m2_m3_m5:NC=1C=CC(=C(C(=O)NCC)C1)[Si](C)(C)C, amount is: 0.0 ;m1_m4_m2_m3_m5:C(C)N(CC)CC, amount is: 0.0 ;m1_m4_m2_m3_m5:C(C1=CC=CC=C1)(=O)Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m6:O, amount is: 0.0 MOLE;m1_m4_m2_m3_m5:C(Cl)Cl, amount is: 0.0 ,Catalysts are m1_m4_m2_m3_m5:CN(C1=CC=NC=C1)C, amount is: 0.0 .Products are 0:C(C1=CC=CC=C1)(=O)NC=1C=CC(=C(C(=O)NCC)C1)[Si](C)(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of the compound of Example 217 (0.118 g, 0.5 mmol) in CH2Cl2 (10 mL) was added triethylamine (0.14 mL, 1.0 mmol), benzoyl chloride (70 μL, 0.6 mmol) and 4-dimethylaminopyridine (12 mg). The reaction was stirred at RT for 16 h, diluted with water, and extracted with ethyl acetate. The extracts were washed with 0.04 N HCl, sat NaHCO3, brine, dried (MgSo4) and concentrated to afford the title compound. The crude product was purified by recrystallization from ethyl acetate/hexanes to afford the title compound as fluffy white crystals (0.129 g, 76%). m.p. 185°-187° C. |
Here is a chemical reaction formula: Reactants are m1_m5_m2_m3:ClC1=C(C(=O)NCC)C(=CC=C1C=O)[Si](C)(C)C, amount is: 0.0 ;m1_m5_m2_m3:[N+](=O)([O-])C, amount is: 0.0 ;m1_m5_m2_m3:[OH-].[Na+], amount is: 0.0 ;m4:Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m5_m2_m3:CO, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC1=C(C(=O)NCC)C(=CC=C1\C=C\[N+](=O)[O-])[Si](C)(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of the compound of Example 223 (0.199 g, 0.7 mmol) in methanol (5 mL) at 0° C. was added nitromethane (0.3 mL, 5.0 mmol) and 2.5 N NaOH (2.3 mL, 5.8 mmol) portionwise over 2 h. The suspension was dissolved by addition of ice-cold water and cold 2N HCl (10 mL) was added. The precipitate was filtered and washed with water to afford the crude title compound. The crude product was purified by recrystallization from aq methanol to afford the title compound as a light yellow fluffy solid (60 mg, 26%). m.p. 104°-106° C. |
Here is a chemical reaction formula: Reactants are m1_m3_m2_m4:S1C(=CC=C1)C(=O)Cl, amount is: 0.0 ;m1_m3_m2_m4:C(C)N, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m3_m2_m4:C(Cl)Cl, amount is: 0.0 ;m1_m3_m2_m4:O, amount is: 0.0 ;m5:O, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:C(C)NC(=O)C=1SC=CC1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 2-thiophenecarboxylic acid chloride (7.3 g, 50 mmol) in 30 mL CH2Cl2 was added to 70% ethylamine in water (11 g) at -5° C. and the resulting solution was stirred at RT for 18 h. After that, water was added. The organic layer was separated, washed with water, brine, dried and concentrated. Purification of the residue by flash chromatography with 25% ethyl acetate-hexane gave 6.4 g (83.1% yield) of N-ethyl-2-thiophenecarboxamide as a white solid, m.p. 75°-78° C. |
Here is a chemical reaction formula: Reactants are m1_m3_m2:C(C)NC(=O)C=1SC(=CC1[Si](C)(C)C)CO, amount is: 0.0 ;m1_m3_m2:[Cr](=O)(=O)([O-])Cl.[NH+]1=CC=CC=C1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2:C(Cl)Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C)NC(=O)C=1SC(=CC1[Si](C)(C)C)C=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To the compound of step b (1.3 g, 5 mmol) in 40 mL CH2Cl2 containing 1.8 g celite was added 2.4 g pyridinium chlorochromate and the resulting reaction mixture was stirred at RT for 2 h. The CH2 Cl2 solution was filtered through celite, washed with water, brine, dried and concentrated in vacuo. The residue was purified by flash chromatography with 10% ethyl acetate-hexane to give 1.1 g of the desired product as a light yellow solid, m.p. 62°-65° C. |
Here is a chemical reaction formula: Reactants are m1_m2_m5_m3:C(C)NC(=O)C=1SC(=CC1[Si](C)(C)C)S(=O)C, amount is: 0.0 ;m1_m2_m5_m3:[Na+].[I-], amount is: 0.0 ;m1_m2_m5_m3:FC(C(=O)OC(C(F)(F)F)=O)(F)F, amount is: 0.0 ;m4:S(=O)(=O)([O-])S(=O)[O-].[Na+].[Na+], amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m2_m5_m3:CC(=O)C, amount is: 0.0 ;m6:C(Cl)Cl, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:C(C)NC(=O)C=1SC(=CC1[Si](C)(C)C)SC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of the compound of Example 260 (0.6 g) and NaI (0.8 g) in 10 mL acetone was added slowly 0.4 mL trifluoroacetic anhydride at 0° C. and the mixture was stirred at 0° C. for an additional hour. Then CH2Cl2 and aq sat sodium meta-bisulfite were added. The organic layer was separated, washed with brine, dried and concentrated. Flash chromatography of the residue with 10% ethyl acetate-hexane gave 0.5 g of the title compound as a white solid. m.p. 58°-61° C. |
Here is a chemical reaction formula: Reactants are m3:C[Si](C)(C)Cl, amount is: 0.0 MOLE;m1_m2:ClC1=CC=C(S1)C(=O)O, amount is: 0.0 MOLE;m1_m2:C(C=C)N, amount is: 0.0 MOLE,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:ClC1=CC(=C(S1)C(=O)NCC=C)[Si](C)(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The title compound was prepared from 5-chloro-2-thiophenecarboxylic acid and allylamine, followed by reaction with TMSCl using the methods of Example 248 to afford 0.7 g of the title compound as a white solid. m.p. 63°-66° C. |
Here is a chemical reaction formula: Reactants are m1_m2_m5_m3:ClC1=CC(=C(S1)C(=O)NCCO)[Si](C)(C)C, amount is: 0.0 ;m1_m2_m5_m3:C(C)N(CC)CC, amount is: 0.0 ;m1_m2_m5_m3:CS(=O)(=O)Cl, amount is: 0.0 ;m4:O, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m2_m5_m3:C(Cl)Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC1=CC(=C(S1)C(=O)NCCOS(=O)(=O)C)[Si](C)(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of the compound of Example 263 (0.4 g) and 0.5 mL triethylamine in 10 mL CH2Cl2 at 0° C. was added methanesulfonyl chloride (0.2 mL) and the resulting reaction solution was stirred at RT for 2 h. Water was added and the two layers were separated. The organic solution was washed with brine, dried and concentrated. Purification by flash chromatography with 30% ethyl acetate-hexane gave 0.4 g of product as a white solid. m.p. 82°-86° C. |
Here is a chemical reaction formula: Reactants are m1_m4_m2_m5:BrC1=CSC=C1Br, amount is: 0.0 ;m1_m4_m2_m5:[Li]C(C)(C)C, amount is: 0.0 ;m6_m3:C(=O)=O, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m4_m2_m5:CCOCC, amount is: 0.0 ;m1_m4_m2_m5:CCCCC, amount is: 0.0 MOLE;m6_m3:CCOCC, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:BrC=1C(=CSC1)C(=O)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 3,4-dibromothiophene (15 g, 62 mmol) in 80 mL ether under a positive nitrogen atmosphere was added dropwise 75 mL 1.7M t-BuLi in pentane at below -73° C. and the resulting reaction solution was stirred at -78° C. for 0.5 h. After that, the ether solution was poured into dry ice and extracted with water. The aq solution was washed with ether and then acidified with concentrated HCl. The solid was filtered and air-dried to give 9 g of 4-bromo-3-thiophenecarboxylic acid, yield 70.3%. |
Here is a chemical reaction formula: Reactants are m0_m1_m2_m3:BrC=1C(=CSC1)C(=O)O, amount is: 0.0 ;m0_m1_m2_m3:C(C)N, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m0_m1_m2_m3:O, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:C(C)NC(=O)C1=CSC=C1Br, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: N-Ethyl-4-bromo-3-thiophenecarboxamide was prepared from 4-bromo-3-thiophenecarboxylic acid (7 g, 34 mmol) and 70% ethylamine in water according to steps a and b of Example 248 in 64.5% yield. |
Here is a chemical reaction formula: Reactants are m0_m1_m2_m3:BrC1=CC(=CS1)C(=O)O, amount is: 0.0 ;m0_m1_m2_m3:C(C)N, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m0_m1_m2_m3:O, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:BrC1=CC(=CS1)C(=O)NCC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 5-Bromo-N-ethyl-3-thiophenecarboxamide was prepared from 5-bromo-3-thiophenecarboxylic acid (2.1 g, 10 mmol) and 70% ethylamine in water according to the methods of steps a and b of Example 248 in 70% yield. |
Here is a chemical reaction formula: Reactants are m1_m2:C(C)NC(=O)C=1C2=C(SC1[Si](C)(C)C)CCCC2, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m2:C(C)C(=O)C, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:CC=1C(=C(SC1C)[Si](C)(C)C)C(=O)NCC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Using the procedures for the synthesis of the compound of Example 270 and methyl ethyl ketone as the starting material, the title compound was obtained as a white solid. m.p. 90°-94° C. |
Here is a chemical reaction formula: Reactants are m1_m2_m4_m3:NC=1C=CC(=C(C(=O)NCC)C1)[Si](C)(C)C, amount is: 0.0 ;m1_m2_m4_m3:N1N=NC2=C1C=CC=C2, amount is: 0.0 ;m1_m2_m4_m3:C=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m4_m3:C(C)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:N1(N=NC2=C1C=CC=C2)CNC=2C=CC(=C(C(=O)NCC)C2)[Si](C)(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of the compound of Example 217 (0.29 g, 1.2 mmol) and benzotriazole (0.143 g, 1.2 mmol) in absolute ethanol (5 mL) at RT was added 37% aq formaldehyde (0.090 mL, 1.2 mmol). An aliquot was induced to precipitate by cooling and addition of a small amount of water. The precipitate was added back into the reaction which was stirred at RT overnight and cooled in a refrigerator for 6 h. The resultant mixture was filtered and dried under vacuum (P2O5) to afford 5-[(1H-benzotriazol-1-ylmethyl)amino]-N-ethyl-2-(trimethylsilyl)benzamide as a white solid (0.308 g, 70%). m.p. 207°-208° C. |
Here is a chemical reaction formula: Reactants are m1_m5_m7_m3_m2:ClC1=C(C(=O)NCC)C(=CC=C1I)[Si](C)(C)C, amount is: 0.0 ;m1_m5_m7_m3_m2:C(=C)[Sn](CCCC)(CCCC)CCCC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m5_m7_m3_m2:C1(=CC=CC=C1)C, amount is: 0.0 ;m4:CCOCC, amount is: 0.0 MOLE,Catalysts are m6:C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Pd], amount is: 0.0 ;m1_m5_m7_m3_m2:C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Pd], amount is: 0.0 ;m1_m5_m7_m3_m2:C(C)(C)(C)C1=C(C(=CC(=C1)C)C(C)(C)C)O, amount is: 0.0 .Products are 0:ClC1=C(C(=O)NCC)C(=CC=C1C=C)[Si](C)(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of the compound of Example 239 (0.382 g, 1.0 mmol), tetrakis(triphenylphosphine)palladium(O) (23 mg, 0.02 mmol) and 2.6-di-t-butyl-4-methylphenol (1.5 mg) in toluene (10 mL) was added vinyltributyltin (0.349 g, 1.1 mmol). The light yellow solution was heated at reflux for 24 h, additional tetrakis(triphenylphosphine)palladium(O) (15 mg) was added, and reflux was continued for 24 h. The cool mixture was diluted with ether, filtered through Celite, concentrated and purified by RC (ethyl acetate/hexanes). The product was further purified by recrystallization from pentane to afford the title compound as white needles (0.060 g, 21%). m.p. 127°-128° C. |
Here is a chemical reaction formula: Reactants are m1_m3:P(=O)(OCC)(OCC)Cl, amount is: 0.0 ;m2:C(C)N, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3:ClC(C)Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C)NP(OCC)(OCC)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 5.0 g (29.0 mmol) of diethyl chlorophosphate in 70 mL dichloroethane cooled on an ice bath was added 4.1 g (63.8 mmol) of ethylamine (70% aq). The mixture was allowed to stir at RT for 30 min and was then partitioned between ether and water. The organic layer was washed with brine, dried (MgSO4), and was filtered. The filtrate was evaporated in vacuo and the residue was kugelrohr distilled (0.8 torr, 90° C.) to yield 2.7 g (52%) of diethyl N-ethylphosphoramidate as a colorless oil. |
Here is a chemical reaction formula: Reactants are m3:ClCSC, amount is: 0.0 ;m1_m5_m2:ClC1=C(C(=O)NCC)C(=CC=C1)[Si](C)(C)C, amount is: 0.0 ;m1_m5_m2:C[Si](C)(C)[N-][Si](C)(C)C.[Na+], amount is: 0.0 ;m4:ClCSC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m5_m2:C1CCOC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC1=C(C(=O)N(CSC)CC)C(=CC=C1)[Si](C)(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 2.0 g (7.8 mmol) of the compound of Example 45 in 30 mL dry THF was added 7.9 mL (7.9 mmol) sodium bis(trimethylsilyl)amide (1.0M in THF). To the resulting mixture was added 1.0 g (10.4 mmol) chloromethyl methylsulfide. The mixture was stirred for 15 min and another 0.65 g (6.7 mmol) of chloromethyl methylsulfide was added. Stirring at RT was continued for 1 h and the mixture was then heated to reflux for 28 hours. The mixture was allowed to cool to RT and was then partitioned between ether and water. The organic layer was washed with brine, dried (MgSO4), and was filtered through silica gel. The filtrate was evaporated in vacuo and the residue was chromatographed (HPLC, 8% ethyl acetate / hexane) to yield 1.1 g (45%) of a colorless oil. nD25 =1.5526. |
Here is a chemical reaction formula: Reactants are m2:OOS(=O)[O-].[K+], amount is: 0.0 MOLE;m3:S(=O)(=O)([O-])S(=O)[O-].[Na+].[Na+], amount is: 0.0 ;m4:O, amount is: 0.0 ;m1:C(C)NC(C1=C(C=CC=C1SC(C)(C)C)F)=O, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m5:CO, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:CC(C)(C)S(=O)(=O)C1=C(C(=O)NCC)C(=CC=C1)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A 0° C. solution of N-ethyl 2-fluoro-6-(1,1-dimethylethylthio)benzamide, described in Example 194, (0.15 g, 0.59 mmol) in methanol (5 mL) was combined with a 0° C. solution of OXONE® (1.08 g, 1.76 mmol) in water (5 mL). This mixture was stirred overnight, then was poured into 25% aq sodium metabisulfite (100 mL) and extracted with ether (3×100 mL). The combined organics were washed with brine followed with water, then was dried (MgSO4) and concentrated to give the title compound as a clear oil. |
Here is a chemical reaction formula: Reactants are m4:CI, amount is: 0.0 ;m1_m2_m3_m5:C(C)N(C(C1=C(C=CC=C1)NC(C)(C)C)=O)CC, amount is: 0.0 ;m1_m2_m3_m5:C([O-])([O-])=O.[K+].[K+], amount is: 0.0 ;m1_m2_m3_m5:CI, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m5:CN(C)C=O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C)N(C(C1=C(C=CC=C1)N(C(C)(C)C)C)=O)CC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of N,N-diethyl-2-(N-tert-butylamino)benzamide (4.2 g, 17 mmol), potassium carbonate (3.1 g, 22 mmol), and MeI (3.1 g, 22 mmol) in DMF (75 mL) was heated overnight at 40° C. The reaction was not complete, so additional MeI (3.1 g, 22 mmol) was added and the reaction heated at 40° C. for 1 d, then was partitioned between EtOAc and water. The EtOAc was dried (MgSO4), concentrated, and purified by HPLC with 1:4 ethyl acetate/cyclohexane to afford 3.22 g of N,N-diethyl-2-(N-methyl-N-tert-butylamino)benzamide as a yellow oil, a 72% yield. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:BrCC(C(=O)OCC)=O, amount is: 0.0 ;m1_m2_m3:NC(=S)N, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3:C(C)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C)OC(=O)C=1N=C(SC1)N, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 90% ethyl bromopyruvate (54.2 g, 0.25 mol) and thiourea (20 g, 0.263 mol) in 500 mL absolute ethanol was heated at reflux for 1 h and then stirred at ambient temperature for 2 h. Ethanol was removed in vacuo and the residue was suspended in ice-water and neutralized with solid potassium carbonate until basic. The solid was filtered, washed thoroughly with water and air-dried to give 42 g of ethyl-2-amino-4-thiazolecarboxylate. |
Here is a chemical reaction formula: Reactants are m6_m1_m5:N(=O)OC(C)(C)C, amount is: 0.0 ;m3_m7_m4:O, amount is: 0.0 MOLE;m3_m7_m4:Cl, amount is: 0.0 ;m2:NC=1SC=C(N1)C(=O)OCC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m6_m1_m5:C(C)#N, amount is: 0.0 ;m3_m7_m4:C(Cl)Cl, amount is: 0.0 MOLE,Catalysts are m6_m1_m5:[Cu](Cl)Cl, amount is: 0.0 .Products are 0:ClC=1SC=C(N1)C(=O)OCC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a mixture of copper (II) chloride (20 g, 0.15 mol) and 90% t-butyl nitrite (24 mL, 0.18 mol) in 500 mL acetonitrile at 60° C. was added in portions ethyl 2-amino-4-thiazolecarboxylate (21 g, 0.12 mol), maintaining the temperature at between 60°-65° C. After the addition, the resulting reaction mixture was heated at 80° C. for 1 h, then cooled to RT and poured into a mixture of water, CH2Cl2 and 25 mL conc HCl. The aq layer was separated and extracted with CH2Cl2. The combined organic layers were washed with water, brine, dried and concentrated to give 21.5 g of ethyl 2-chloro-4-thiazolecarboxylate. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:[OH-].[Na+], amount is: 0.0 ;m1_m2_m3:C(C)OC(=O)C=1N=C(SC1)Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3:C(C)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC=1SC=C(N1)C(=O)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of NaOH (1.9 g, 47.5 mmol) and ethyl-2-chloro-4-thiazolecarboxylate (7.6 g, 40 mmol) in 100 mL absolute ethanol was stirred at RT for 4 h. After that, ethanol was removed in vacuo and the residue was dissolved in water. The aq layer was washed with ether and then acidified with conc HCl. The solid was filtered and air dried to give 4 g of 2-chloro-4-thiazolecarboxylic acid. |
Here is a chemical reaction formula: Reactants are m6_m4_m5:C(C)N, amount is: 0.0 MOLE;m1_m2_m3:ClC=1SC=C(N1)C(=O)Cl, amount is: 0.0 MOLE;m1_m2_m3:ClC=1SC=C(N1)C(=O)O, amount is: 0.0 MOLE;m1_m2_m3:S(=O)(Cl)Cl, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m6_m4_m5:O, amount is: 0.0 MOLE;m6_m4_m5:CN(C)C=O, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:ClC=1SC=C(N1)C(=O)NCC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 2-Chloro-4-thiazolecarboxylic acid chloride (prepared from 2-chloro-4-thiazolecarboxylic acid, thionyl chloride and a catalytic amount of DMF) was reacted with 70% ethylamine in water to yield 2-chloro-N-ethyl-4-thiazolecarboxamide. This compound was reacted with TMSCl using the method of step c of Example 248. Purification by flash chromatography with 3% ethyl acetate-hexane gave 2.5 g of the title compound as a light yellow oil in 55.6% yield. nD26 1.5313. |
Here is a chemical reaction formula: Reactants are m1_m2_m5_m3:N1N=CC=C1, amount is: 0.0 ;m1_m2_m5_m3:C(C)N(CC)CC, amount is: 0.0 ;m1_m2_m5_m3:C(C)N=C=O, amount is: 0.0 ;m6_m4:Cl, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m2_m5_m3:C1CCOC1, amount is: 0.0 ;m6_m4:C(C)(=O)OCC, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:C(C)NC(=O)N1N=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of pyrazole (1.7 g, 25 mmol) and 4 mL triethylamine in 50 mL dry THF was added ethyl isocyanate (2 g, 28 mmol) at 0° C. and the resulting reaction solution was stirred at RT for 18 h. Ethyl acetate and 2N HCl were added. The aq layer was separated and extracted with ethyl acetate. The combined ethyl acetate layers were washed with brine, dried and concentrated in vacuo to give an oil. The oil was triturated with cold hexane to give 2.5 g of N-ethyl-1H-pyrazole-1-carboxamide as a white solid. |
Here is a chemical reaction formula: Reactants are m0_m1:C(C)(C)(C)C1=C(C(=O)Cl)C=CC=C1, amount is: 0.0 MOLE;m2_m3:C(C)N, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m2_m3:O, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:C(C)(C)(C)C1=C(C(=O)NCC)C=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 2-tert-butyl-N-ethylbenzamide was prepared from 2-tert-butylbenzoyl chloride, prepared in Example 186, and 70% ethylamine in water according to the method of step b of Example 248. |
Here is a chemical reaction formula: Reactants are m9_m5:Cl, amount is: 0.0 MOLE;m1_m2_m6_m3_m7:C(C)(C)(C)C1=C(C(=O)NCC)C=CC=C1, amount is: 0.0 ;m1_m2_m6_m3_m7:CN(C)CCN(C)C, amount is: 0.0 ;m1_m2_m6_m3_m7:[Li]C(C)CC, amount is: 0.0 ;m4_m8:ClC(C(Cl)(Cl)Cl)(Cl)Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m9_m5:C(Cl)Cl, amount is: 0.0 MOLE;m1_m2_m6_m3_m7:C1CCOC1, amount is: 0.0 ;m1_m2_m6_m3_m7:C1CCCCC1, amount is: 0.0 MOLE;m10:O, amount is: 0.0 MOLE;m4_m8:C1CCOC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC1=C(C(=O)NCC)C(=CC=C1)C(C)(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 2-tert-butyl-N-ethylbenzamide (44 g, 215 mmol) and TMEDA (70 mL, 446 mmol) in 500 mL THF at -70° C. under a positive nitrogen atmosphere was added at a rapid stream 520 mL 1.3M s-BuLi in cyclohexane, maintaining the temperature at below -60° C. After the addition was complete, the resulting reaction solution was warmed to -30° C. and stirred at between -30° C. and -26° C. for 50 min. The solution was then cooled to below -70° C. and a solution of hexachloroethane (80 g) in 250 mL THF was added at between -70° and -65° C. Stirring at below -70° C. was continued for 0.5 h. The resulting reaction solution was then poured into water. CH2Cl2 and 3N HCl were added. The aq layer was separated and extracted with CH2Cl2. The combined organic layers were washed with water, dried and concentrated in vacuo. The solid was triturated with hexane and then purified by flash chromatography with 15% ethyl acetate/hexane as eluent to give the desired product as a white solid. m.p. 121°-123° C. |
Here is a chemical reaction formula: Reactants are m0_m2_m3:ClC1=CC(=C(S1)C(=O)O)[Si](C)(C)C, amount is: 0.0 ;m0_m2_m3:S(=O)(Cl)Cl, amount is: 0.0 ;m4_m5_m7_m8:Cl.C(C)(C)NO, amount is: 0.0 ;m4_m5_m7_m8:C(=O)(O)[O-].[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m4_m5_m7_m8:C(Cl)Cl, amount is: 0.0 ;m4_m5_m7_m8:O, amount is: 0.0 ;m6:C(Cl)Cl, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:ClC1=CC(=C(S1)C(=O)Cl)[Si](C)(C)C;0:ClC1=CC(=C(S1)C(=O)N(C(C)C)O)[Si](C)(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 5-Chloro-3-(trimethylsilyl)-2-thiophenecarboxylic acid chloride was prepared by the reaction of 1 g 5-chloro-3-(trimethylsilyl)-2-thiophenecarboxylic acid (prepared as in Example 263) and 6 mL thionyl chloride, using the procedure of step a in Example 248. This product was dissolved in CH2Cl2 at 0° C. and added to a mixture of N-isopropylhydroxylamine hydrochloride (0.55g, 5 mmol) and 4 g NaHCO3 in 20 mL CH2Cl2 and 20 mL water. The resulting reaction mixture was stirred at RT for additional 3 h. The organic layer was separated, washed with brine, dried and concentrated. The residue was purified by flash chromatography with 8% ethyl acetate/hexane to give 80 mg of the title compound. m.p. 146°-150° C. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:C(C)OC=C(C(=O)OCC)C#N, amount is: 0.0 ;m1_m2_m3:CNN, amount is: 0.0 ;m1_m2_m3:C(C)O, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:NC1=C(C=NN1C)C(=O)OCC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of ethyl (ethoxymethylene)cyanoacetate (68 g, 0.4 mol) and methylhydrazine (18.5 g, 0.4 mol) in 200 mL absolute ethanol was refluxed for 1.5 h, then cooled to RT and filtered. The filtrate was concentrated in vacuo and the residue was triturated with ether to give 54 g of crude ethyl 5-amino-1-methyl-1H-pyrazole-4-carboxylate in 75.4% yield. |
Here is a chemical reaction formula: Reactants are m1_m5_m2:N(=O)OC(C)(C)C, amount is: 0.0 ;m1_m5_m2:NC1=C(C=NN1C)C(=O)OCC, amount is: 0.0 ;m3_m4:Cl, amount is: 0.0 ;m3_m4:O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m5_m2:CN(C)C=O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:CN1N=CC(=C1)C(=O)OCC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 90% t-butyl nitrite (50 mL, 0.37 mol) in 200 mL DMF was added in portions ethyl 5-amino-1-methyl-1H-pyrazole-4-carboxylate (39 g, 0.23 mol), maintaining the temperature at around 30° C. After the addition, the resulting mixture was warmed to 50° C. and stirred at that temperature for 0.5 h. The mixture was poured into 100 mL conc HCl and 40 mL water and extracted with CH2Cl2. The organic solution was washed with water, brine, dried and concentrated. Vacuum distillation of the residue gave 32.4 g of ethyl 1-methyl-1H-pyrazole-4-carboxylate as a clear liquid. b.p. 65°-80° C. at 0.1 torr. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:CN1N=CC(=C1)C(=O)OCC, amount is: 0.0 ;m1_m2_m3:[OH-].[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3:C(C)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:CN1N=CC(=C1)C(=O)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of ethyl 1-methyl-1H-pyrazole-4-carboxylate (20.2 g, 131 mmol) and NaOH (6.3 g, 158 mmol) in 200 mL absolute ethanol was refluxed for 2 h and stirring was continued at RT for 18 h. After that, the solvent was removed in vacuo. The residue was dissolved in water. The aq solution was washed with ether and acidified with concentrated HCl. The solid was filtered, washed with water and air-dried to give 14.2 g of 1-methyl-1H-pyrazole-4-carboxylic acid in 86% yield. |
Here is a chemical reaction formula: Reactants are m0_m1_m2_m3:CN1N=CC(=C1)C(=O)O, amount is: 0.0 MOLE;m0_m1_m2_m3:C(C)N, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m0_m1_m2_m3:O, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:C(C)NC(=O)C=1C=NN(C1)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: N-Ethyl-1-methyl-1H-pyrazole-4-carboxamide was prepared from 1-methyl-1H-pyrazole-4-carboxylic acid and 70% ethylamine in water using the methods of steps a and b of Example 248. The product was purified by flash chromatography with 10% ethyl acetate-hexane and recovered as a white solid in 54.7% yield. m.p. 103°-106 ° C. |
Here is a chemical reaction formula: Reactants are m2:N1C=NC=C1, amount is: 0.0 ;m3:[Si](C)(C)(C(C)(C)C)Cl, amount is: 0.0 ;m1:C(CCCCCCCCCCCCCCCCCCCCCO)O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m4:CN(C)C=O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:[Si](C)(C)(C(C)(C)C)OCCCCCCCCCCCCCCCCCCCCCCO, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 1,22-Docosanediol 1 (2.00 g, 5.84 mmol) and imidazole (0.817 g, 12.0 mmol) were placed in each of two nitrogen-purged 150 mL three-necked flasks fitted with a thermometer and magnetic stir bar. The flasks were resealed and purged with nitrogen. Dimethylformamide (40 mL) was added to each flask and the cloudy mixtures were heated until they became homogenous at 63° C. tert-Butyldimethylsilyl chloride (0.904 g, 6.00 mmol, in 10 mL DMF) was slowly added to the reaction mixture (the transfer was aided with an additional 5 mL of DMF) and the mixture was allowed to react for 24 hours at 60°-65° C. The solutions were cooled down to room temperature and filtered to recover starting material using water (25 mL) to aid in transfer. The filtrate was diluted with water (300 mL) and extracted with methylene chloride (500 mL). The organic layer was dried (Na2SO4) and concentrated. A very low mass balance led to the discovery that much of the desired material was contained in the recovered solid that had been previously filtered off. None of the desired compound was found in the aqueous wash by TLC. The recovered solid was suspended in methylene chloride (100 mL), stirred, and refiltered. The filtrate was combined with the previously isolated material and concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 10% ethyl acetate/hexane). Concentration of the desired fractions using acetone to reduce violent bumping yielded the desired material 2 as a white solid (2.22 g, 46.7%). |
Here is a chemical reaction formula: Reactants are m1_m2_m5:CSC1=CC=C(C=C1)[N+](=O)[O-], amount is: 0.0 ;m1_m2_m5:O, amount is: 0.0 ;m3:S(=O)(=O)(Cl)Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m5:ClC1=CC=CC=C1, amount is: 0.0 ;m4:ClC1=CC=CC=C1, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:[N+](=O)([O-])C1=CC=C(C=C1)S(=O)(=O)Cl, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A 2-liter, 4-necked flask equipped with a stirrer, thermometer, condenser and a dropping funnel having a by-pass was charged with 20.4 g (0.10 mole) of 4-nitrophenyl methyl sulfide, 10 g of water and 200 g of monochlorobenzene. Then, 94.5 g (0.70 mole) of sulfuryl chloride was added dropwise at 10° C. over a period of about 2 hours. Thereafter the mixture was stirred at 10° C. for 6 hours to complete the reaction. After completion of the reaction, the oil layer was separated and 10 g of water was added to accomplish washing. Then, the oil layer was separated and left to stand for about 1 hour with the addition of about 5 g of anhydrous sodium sulfate to remove the water. The solvent was distilled off to give crude crystals. The crude crystals were dissolved in monochlorobenzene and a poor solvent was added for recrystallization, giving 21.1 g of 4-nitrobenzenesulfonyl chloride as white crystals in a yield of 95% as calculated based on 4-nitrophenyl methyl sulfide. |
Here is a chemical reaction formula: Reactants are m1:C(C=C)(=O)O, amount is: 0.0 MOLE;m2:S(O)(O)(=O)=O, amount is: 0.0 MOLE;m3:COC1=CC=C(O)C=C1, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m5:C(CCC)O, amount is: 0.0 MOLE;m7:C(CCC)O, amount is: 0.0 MOLE;m6:C(CCC)O, amount is: 0.0 MOLE;m4:C(CCC)O, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:C(C=C)(=O)OCCCC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: For comparison, a known esterification process was carried out using only one reaction region. In this Comparative Example, 4 mol/h of acrylic acid, 4 mol/h of fresh butanol and 1.6 mol/h of recycled butanol (distillate from the butanol recovery) were fed to a circulation evaporator (2.5 l, level of fill 2 l). The residence time was 2.5 h. The esterification was carried out in the presence of 9.7% by weight (based on the reaction mixture) of sulfuric acid at 126° C. The reactor was connected to a bubble-cap column (30 trays), which was stabilized with 15 ml/h of hydroquinone monomethyl ether (MeHQ) in butanol. Butyl acrylate formed was removed via the top by adding 340 ml/h of water as a reflux (azeotropic entraining agent) to the column. In addition, 175 ml/h of organic reflux were added to the column in order to suppress the acrylic acid. |
Here is a chemical reaction formula: Reactants are m1:C(=C)P(O)(O)=O, amount is: 0.0 MOLE;m2_m3:P(Cl)(Cl)Cl, amount is: 0.0 MOLE;m2_m3:C1CO1, amount is: 0.0 MOLE;m4:P(OCCCl)(OCCCl)OCCCl, amount is: 0.0 MOLE,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:ClCCP(OCCCl)(OCCCl)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Vinylphosphonic acid, CH2 =CH--PO(OH)2, can be prepared in a known manner by the following method: Phosphorus trichloride is reacted with ethylene oxide, the resulting tris(2-chloroethyl) phosphite is rearranged to give bis(2-chloroethyl) 2-chloroethylphosphonate, followed by reaction of the bis(2-chloroethyl) 2-chloroethylphosphonate with phosgene in the presence of suitable catalysts to give 2-chloroethylphosphonic dichloride (German Patent No. 2,132,962). The 2-chloroethylphosphonic dichloride can then be converted into vinylphosphonic acid by eliminating HCl in the presence of suitable catalysts (BaCl2) and subsequent hydrolysis of the vinylphosphonic dichloride formed (Chem. Abstr. 54, page 265 (1960)). |
Here is a chemical reaction formula: Reactants are m3:ClN1C(CCC1=O)=O, amount is: 0.0 ;m4:[OH-].[Na+], amount is: 0.0 MOLE;m1_m6_m2:FC1=C(N)C=C(C(=C1)F)F, amount is: 0.0 ;m1_m6_m2:CSC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m5:C(C)N(CC)CC, amount is: 0.0 ;m1_m6_m2:ClCCl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:CSCC1=C(N)C(=CC(=C1F)F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To 2,4,5-trifluoroaniline (35.0 g) are added anhydrous dichloromethane (530 ml) and dimethyl sulfide (24.6 ml) and the mixture is cooled to 0° C. Thereto N-chlorosuccinimide (38.2 g) is gradually added below 5° C. After the mixture is stirred at the same temperature for 15 minutes, triethylamine (47.7 ml) is gradually added. After reflux for 12 hours, the resultant is made alkaline with 5% aqueous sodium hydroxide solution, extracted with dichloromethane, and the extract is dried over sodium sulfate and concentrated. The residue is purified with column chlomatography (silica-gel, dichloromethane:n-hexane=1:4) to give 2-methylthiomethyl-3,4,6-trifluoroaniline (22.3 g). |
Here is a chemical reaction formula: Reactants are m1_m3_m2:CSCC1=C(N)C(=CC(=C1F)F)F, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2:C(C)O, amount is: 0.0 ,Catalysts are m1_m3_m2:[Ni], amount is: 0.0 .Products are 0:CC1=C(N)C(=CC(=C1F)F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To 2-methylthiomethyl-3,4,6-trifluoroaniline (22.2 g) are added ethanol (400 ml) and Raney nickel (200 g) and the mixture is stirred at room temperature for 30 minutes. After the catalyst is filtered off, the filtrate is added with water and extracted with dichloromethane. The is dried over magnesium sulfate and concentrated to give 2-methyl-3,4,6-trifluoroaniline (12.3 g). |
Here is a chemical reaction formula: Reactants are m3:N(=O)[O-].[Na+], amount is: 0.0 ;m2_m8:S(O)(O)(=O)=O, amount is: 0.0 ;m1:CC1=C(N)C(=CC(=C1F)F)F, amount is: 0.0 ;m6_m4_m5_m7:[C-]#N.[K+], amount is: 0.0 ;m6_m4_m5_m7:[OH-].[NH4+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m2_m8:O, amount is: 0.0 ;m6_m4_m5_m7:O, amount is: 0.0 ,Catalysts are m6_m4_m5_m7:S(=O)(=O)([O-])[O-].[Cu+2], amount is: 0.0 .Products are 0:CC1=C(C#N)C(=CC(=C1F)F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To 2-methyl-3,4,6-trifluoroaniline (10.6 g) is added a mixture of conc. sulfuric acid (13.8 ml) and water (46 ml) and the mixture is cooled. Thereto an aqueous solution (20 ml) of sodium nitrite (5.5 g) is added dropwise at 0°-5° C. The solution is gradually added to a mixture of copper (II) sulfate 5 hydrate (41 g), potassium cyanide (43 g), ammonium hydroxide (60 ml) and water (260 ml) at 10°-30° C. The mixture is extracted with dichloromethane and the extract is dried over sodium sulfate, concentrated and the residue is purified with column chromatography (silica-gel, dichloromethane:n-hexane=1:4) to give 2-methyl-3,4,6-trifluorobenzonitrile (4.3 g). |
Here is a chemical reaction formula: Reactants are m1_m2:CC1=C(C(=O)O)C(=CC(=C1F)F)F, amount is: 0.0 ;m1_m2:S(=O)(Cl)Cl, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:CC1=C(C(=O)Cl)C(=CC(=C1F)F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To 2-methyl-3,4,6-trifluorobenzoic acid (3.2 g) is added thionyl chloride (7 ml) and the mixture is refluxed for 1 hour. After concentrating, 2-methyl-3,4,6-trifluorobenzoyl chloride (3.3 g) is obtained. |
Here is a chemical reaction formula: Reactants are m4_m10:S(O)(O)(=O)=O, amount is: 0.0 ;m5_m1_m6:[Mg], amount is: 0.0 ;m3_m7:CC1=C(C(=O)Cl)C(=CC(=C1F)F)F, amount is: 0.0 MOLE;m2_m9_m8:C(CC(=O)OCC)(=O)OCC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m4_m10:O, amount is: 0.0 ;m5_m1_m6:C(C)O, amount is: 0.0 ;m3_m7:C1(=CC=CC=C1)C, amount is: 0.0 ;m2_m9_m8:C1(=CC=CC=C1)C, amount is: 0.0 ;m2_m9_m8:C(C)O, amount is: 0.0 ,Catalysts are m5_m1_m6:C(Cl)(Cl)(Cl)Cl, amount is: 0.0 MOLE.Products are 0:CC1=C(C(=O)C(C(=O)OCC)C(=O)OCC)C(=CC(=C1F)F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Separately, two drops of carbon tetrachloride are added to a solution of metallic magnesium (0.4 g) in absolute ethanol (0.9 ml). When the reaction starts, a mixture of diethyl malonate (2.6 ml), absolute ethanol (1.6 ml) and anhydrous toluene (6 ml) is added dropwise below 60° C. After stirring at 60° C. for 1 hour, the reaction mixture is cooled to 0° C. and thereto a solution of 2-methyl-3,4,6-trifluorobenzoyl chloride prepared above in toluene (5 ml) is added dropwise. After stirring for 30 minutes, a mixture of conc. sulfuric acid (0.4 ml) and water (6 ml) is added and the mixture is extracted with diethyl ether, and the extract is dried over magnesium sulfate and concentrated to give diethyl 2-methyl-3,4,6-trifluorobenzoylmalonate (5.2 g). |
Here is a chemical reaction formula: Reactants are m1_m3_m2:CC1=C(C(=O)C(C(=O)OCC)C(=O)OCC)C(=CC(=C1F)F)F, amount is: 0.0 ;m1_m3_m2:C1(=CC=C(C=C1)S(=O)(=O)O)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2:O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:CC1=C(C(=O)CC(=O)OCC)C(=CC(=C1F)F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To diethyl 2-methyl-3,4,6-trifluorobenzoylmalonate (5.1 g) are added water (20 ml) and p-toluenesulfonic acid (30 mg) and the mixture is refluxed for 2.5 hours. After cooling, the resultant is extracted with diethyl ether, and the extract is dried over magnesium sulfate and concentrated to give ethyl 2-methyl-3,4,6-trifluorobenzoylacetate (3.3 g). |
Here is a chemical reaction formula: Reactants are m1_m2_m3:CC1=C(C(=O)CC(=O)OCC)C(=CC(=C1F)F)F, amount is: 0.0 ;m1_m2_m3:C(C)(=O)OC(C)=O, amount is: 0.0 ;m1_m2_m3:C(C)OC(OCC)OCC, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:CC1=C(C(=O)C(C(=O)OCC)=COCC)C(=CC(=C1F)F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To ethyl 2-methyl-3,4,6-trifluorobenzoylacetate (3.2 g) are added acetic anhydride (3.0 g) and triethoxymethane (2.7 g) and the mixture is refluxed for 1 hour. After concentrating, ethyl 2-(2-methyl-3,4,6-trifluorobenzoyl)-3-ethoxyacrylate (3.5 g) is obtained. |
Here is a chemical reaction formula: Reactants are m1_m3:CC1=C(C(=O)C(C(=O)OCC)=COCC)C(=CC(=C1F)F)F, amount is: 0.0 ;m2:C1(CC1)N, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3:C(C)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:CC1=C(C(=O)C(C(=O)OCC)=CNC2CC2)C(=CC(=C1F)F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Ethyl 2-(2-methyl-3,4,6-trifluorobenzoyl)-3-ethoxyacrylate (3.5 g) is dissolved in ethanol (25 ml) and thereto cyclopropylamine (0.84 ml) is added dropwise under ice-cooling. After stirring at room temperature for 30 minutes, the mixture is concentrated and the residue is purified with column chromatography (silica-gel, dichloromethane:n-hexane=1:1) to give ethyl 2-(2-methyl-3,4,6-trifluorobenzoyl)-3-cyclopropylaminoacrylate (2.7 g). |
Here is a chemical reaction formula: Reactants are m1_m3_m2:C1(CC1)N1C=C(C(C2=C(C(=C(C=C12)F)F)C)=O)C(=O)OCC, amount is: 0.0 ;m1_m3_m2:Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2:C(C)(=O)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C1(CC1)N1C=C(C(C2=C(C(=C(C=C12)F)F)C)=O)C(=O)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To ethyl 1-cyclopropyl-6,7-difluoro-5-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylate (1.9 g) are added 90% acetic acid (20 ml) and conc. hydrochloric acid (5 ml) and the mixture is refluxed for 2 hours. After cooling, the precipitated crystals are isolated, washed with water, ethanol, and diethyl ether in this order to give 1-cyclopropyl-6,7-difluoro-5-methyl-1,4,-dihydro-4-oxoquinoline-3-carboxylic acid (1.6 g), as colorless needles, m.p. 294°-298° C. |
Here is a chemical reaction formula: Reactants are m2:FC1=CC=C(N)C=C1, amount is: 0.0 ;m1:CC1=C(C(=O)C(C(=O)OCC)=COCC)C(=CC(=C1F)F)F, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:CC1=C(C(=O)C(C(=O)OCC)=CNC2=CC=C(C=C2)F)C(=CC(=C1F)F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Employing ethyl 2-(2-methyl-3,4,6-trifluorobenzoyl)-3-ethoxyacrylate (1.0 g) and p-fluoroaniline (0.39 g), the procedure of Reference Example 8 is repeated to give ethyl 2-(2-methyl-3,4,6-trifluorobenzoyl)-3-(4-fluorophenyl)aminoacrylate, which is then treated with 60% sodium hydride (0.15 g) as in Reference Example 9 to give ethyl 1-(4-fluorophenyl)-5-methyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate (0.64 g), as white crystals (recrystallized from ethanol), m.p. 256°-259° C. |
Here is a chemical reaction formula: Reactants are m2:Cl, amount is: 0.0 ;m1:FC1=CC=C(C=C1)N1C=C(C(C2=C(C(=C(C=C12)F)F)C)=O)C(=O)OCC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m3:C(C)(=O)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:FC1=CC=C(C=C1)N1C=C(C(C2=C(C(=C(C=C12)F)F)C)=O)C(=O)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Employing ethyl 1-(4-fluorophenyl)-5-methyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate (0.56 g), conc. hydrochloric acid (1.5 ml), and 90% acetic acid (6 ml), the procedure of Reference Example 10 is repeated to give 1-(4-fluorophenyl)-5-methyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (0.49 g), as white crystals, m.p. 255°-257° C. |
Here is a chemical reaction formula: Reactants are m2:C(C)N, amount is: 0.0 ;m1:CC1=C(C(=O)C(C(=O)OCC)=COCC)C(=CC(=C1F)F)F, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:CC1=C(C(=O)C(C(=O)OCC)=CNCC)C(=CC(=C1F)F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Employing ethyl 2-(2-methyl-3,4,6-trifluorobenzoyl)-3-ethoxyacrylate (1.0 g) and 70% aqueous ethylamine solution (0.24 ml), the procedure of Reference Example 8 is repeated to give ethyl 2-(2-methyl-3,4,6-trifluorobenzoyl)-3-ethylaminoacrylate, which is then treated with 60% sodium hydride (0.15 g) as in Reference Example 9 to give ethyl 1-ethyl-5-methyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate (0.6 g), as white crystals, m.p. 157°-159° C. |
Here is a chemical reaction formula: Reactants are m2:Cl, amount is: 0.0 ;m1:C(C)N1C=C(C(C2=C(C(=C(C=C12)F)F)C)=O)C(=O)OCC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m3:C(C)(=O)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C)N1C=C(C(C2=C(C(=C(C=C12)F)F)C)=O)C(=O)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Employing ethyl 1-ethyl-5-methyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate (0.55 g), conc. hydrochloric acid (1.5 ml) and 90% acetic acid (6 ml), the procedure of Reference Example 10 is repeated to give 1-ethyl-5-methyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (0.40 g), as white crystals, m.p.>300° C. |
Here is a chemical reaction formula: Reactants are m1:CC1=C(C(=O)C(C(=O)OCC)=COCC)C(=CC(=C1F)F)F, amount is: 0.0 ;m2:FC1=C(N)C=CC(=C1)F, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:CC1=C(C(=O)C(C(=O)OCC)=CNC2=C(C=C(C=C2)F)F)C(=CC(=C1F)F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Employing ethyl 2-(2-methyl-3,4,6-trifluorobenzoyl)-3-ethoxyacrylate (1.0 g) and 2,4-difluoroaniline (0.5 g), the procedure of Reference Example 8 is repeated to give ethyl 2-(2-methyl-3,4,6-trifluorobenzoyl)-3-(2,4-difluorophenyl)aminoacrylate (1.1 g). |
Here is a chemical reaction formula: Reactants are m1:CC1=C(C(=O)C(C(=O)OCC)=CNC2=C(C=C(C=C2)F)F)C(=CC(=C1F)F)F, amount is: 0.0 ;m2:[H-].[Na+], amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:FC1=C(C=CC(=C1)F)N1C=C(C(C2=C(C(=C(C=C12)F)F)C)=O)C(=O)OCC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Employing ethyl 2-(2-methyl-3,4,6-trifluorobenzoyl)-3-(2,4-difluorophenyl)aminoacrylate (1.1 g) and 60% sodium hydride (0.13 g), the procedure of Reference Example 9 is repeated to give ethyl 1-(2,4-difluorophenyl)-5-methyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate (0.7 g). |
Here is a chemical reaction formula: Reactants are m1_m2:N1(CCNCC1)C=1C=C(NC2CC2)C(=C(C1F)C)[N+](=O)[O-], amount is: 0.0 ;m1_m2:C(C)OC=C(C(=O)OCC)C(=O)OCC, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:C1(CC1)N(C1=CC(=C(C(=C1[N+](=O)[O-])C)F)N1CCNCC1)C=C(C(=O)OCC)C(=O)OCC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To 3-(1-piperazinyl)-4-fluoro-5-methyl-6-nitro-N-cyclopropylaniline (1.57 g) is added diethyl ethoxymethylenemalonate (1.45 ml) and the mixture is heated at 150° C. for 25 hours. After cooling, the reaction product is purified by silica-gel column-chromatography (dichloromethane:methanol=100:1) to give diethyl [N-cyclopropyl-N-[3-(1-piperazinyl)-4-fluoro-5-methyl-6-nitrophenyl]aminomethylene]malonate (1.50 g). The product is dissolved in acetic anhydride (7.9 ml) and thereto conc. sulfuric acid (3.16 ml) is added dropwise at 50°-60° C., followed by stirring for 30 minutes. The resultant mixture is poured into ice-water, neutralized, extracted with dichloromethane and the extract is dried. The solvent is distilled off under reduced pressure. Purification by silica-gel column-chromatography (dichloromethane:methanol=10:1) to give ethyl 7-(1-piperazinyl)-1-cyclopropyl-6-fluoro-5-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylate (26 mg). |
Here is a chemical reaction formula: Reactants are m1_m3_m2:C(C)(C)(C)OC(=O)NC1CN(CC1C)C1=C(C(=C2C(C(=CN(C2=C1)C1CC1)C(=O)O)=O)C)F, amount is: 0.0 ;m1_m3_m2:Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2:C(C)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:Cl.NC1CN(CC1C)C1=C(C(=C2C(C(=CN(C2=C1)C1CC1)C(=O)O)=O)C)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture comprising 7-(3-t-butoxycarbonylamino-4-methyl-1-pyrrolidinyl)-1-cyclopropyl-6-fluoro-5-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (trans form) (120 mg), ethanol (4 ml) and 10% hydrochloric acid (4 ml) is refluxed for 30 minutes. After concentrating, the obtained residue is recrystallized from methanol - ethyl acetate to give 7-(3-amino-4-methyl-1-pyrrolidinyl)-1-cyclopropyl-6-fluoro-5-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid hydrochloride (trans form) (60 mg), as white powder, m.p. 272°-275° C. |
Here is a chemical reaction formula: Reactants are m1_m4_m2:N1(CCNCC1)C1=C(C(=C2C(C(=CN(C2=C1)C1CC1)C(=O)O)=O)C)F, amount is: 0.0 ;m1_m4_m2:C(C)(=O)OC(C)=O, amount is: 0.0 ;m3:Cl, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m4_m2:[OH-].[Na+], amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C)(=O)N1CCN(CC1)C1=C(C(=C2C(C(=CN(C2=C1)C1CC1)C(=O)O)=O)C)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 7-(l-piperazinyl)-1-cyclopropyl-6-fluoro-5-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (40 mg) in 5% sodium hydroxide (2 ml) is added acetic anhydride (0.1 ml) at room temperature. After the mixture is made acidic with dilute hydrochloric acid, the resultant is extracted with dichloromethane and the extract is dried over magnesium sulfate. After concentrating, the obtained residue is recrystallized from ethanol to give 7-(4-acetyl-1-piperazinyl)-1-cyclopropyl-6-fluoro-5-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (29 mg), as white powder, m.p. 261°-263° C. |
Here is a chemical reaction formula: Reactants are m1_m3_m2:C1(CC1)N1C=C(C(C2=C(C(=C(C=C12)Br)F)C)=O)C(=O)O, amount is: 0.0 ;m1_m3_m2:O=C1CCNCC1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2:CN1C(CCC1)=O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C1(CC1)N1C=C(C(C2=C(C(=C(C=C12)N1CCC(CC1)=O)F)C)=O)C(=O)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 1-cyclopropyl-6-fluoro-7-bromo-5-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (0.58 g) in N-methyl-2-pyrrolidone (5 ml) is added 4-oxopiperidine (0.64 g) and the mixture is heated at 90° C. for 20 minutes. The solvent is distilled off under reduced pressure. To the resulting residue is added ethanol and the precipitated crystals are filtered to give 1-cyclopropyl-6-fluoro-7-(4-oxo-1-piperidinyl)-5-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (230 mg). |
Here is a chemical reaction formula: Reactants are m1:BrC(C(CC(=O)O)(F)Cl)(F)F, amount is: 0.0 MOLE,this reaction does not need reagents,this reaction does not need solvents,Catalysts are m2:[Zn], amount is: 0.0 MOLE.Products are 0:FC(CC(=O)O)=C(F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Dehalogenation of 4-bromo-3-chloro-3,4,4-trifluorobutanoic acid (VIII) with zinc using conditions analogous to those disclosed in the literature to obtain the desired 3,4,4-trifluoro-3-butenoic acid (IV); or |
Here is a chemical reaction formula: Reactants are m2_m3_m4_m5_m6:ClC(C(Br)(F)F)(Br)F, amount is: 0.0 MOLE;m2_m3_m4_m5_m6:ClC(C(Cl)(F)F)(Cl)F, amount is: 0.0 MOLE;m2_m3_m4_m5_m6:C(=C)(Cl)Cl, amount is: 0.0 MOLE;m2_m3_m4_m5_m6:S(=O)(=O)([O-])OOS(=O)(=O)[O-].[NH4+].[NH4+].C(=O)[O-].[Na+], amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m2_m3_m4_m5_m6:CN(C)C=O, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:BrC(C(CC(=O)O)(F)Cl)(F)F;0:ClC(CC(=O)O)(C(F)(F)Cl)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A one pot reaction of 1-chloro-1,2-dibromotrifluoroethane (VI) or 1,1,2-trichlorotrifluoroethane (X) with vinylidene chloride in the presence of ammonium persulfate/sodium formate/air in DMF to give 4-bromo-3-chloro-3,4,4-trifluorobutanoic acid (VIII) or 3,4-dichloro-3,4,4-trifluorobutanoic acid (XI). |
Here is a chemical reaction formula: Reactants are m1_m2_m3:FC(CC(=O)O)=C(F)F, amount is: 0.0 MOLE;m1_m2_m3:C(C(=O)Cl)(=O)Cl, amount is: 0.0 MOLE,this reaction does not need reagents,this reaction does not need solvents,Catalysts are m1_m2_m3:CN(C)C=O, amount is: 0.0 MOLE.Products are 0:FC(CC(=O)Cl)=C(F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Reaction of 3,4,4-trifluoro-3-butenoic acid (IV) with oxalyl chloride in the presence of DMF as a catalyst without any solvent to give 3,4,4-trifluoro-3-butenoyl chloride (V). |
Here is a chemical reaction formula: Reactants are m1_m3_m2:FC(CCO)=C(F)F, amount is: 0.0 MOLE;m1_m3_m2:CC(=O)C.OS(=O)(=O)O.O=[Cr](=O)=O, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m3_m2:CC(=O)C, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:FC(CC(=O)O)=C(F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The first method involves hydrolysis of 4-bromo-1,1,2-trifluoro-1butene (II) with water in the presence of N-methyl pyrrolidinone to give 3,4,4-trifluoro-3-buten-1-ol (III), followed by Jones oxidation under conditions not previously known. These conditions are at a temperature of about 51°-54° C. In addition, the 3,4,4-trifluoro-3-buten-1-ol in acetone solvent and the Jones reagent are added to the reaction vessel simultaneously to afford 3,4,4-trifluoro-3-butenoic (IV) acid in 52% overall yield. ##STR3## |
Here is a chemical reaction formula: Reactants are m1:BrC(C(CC(=O)O)(F)Cl)(F)F, amount is: 0.0 MOLE,this reaction does not need reagents,this reaction does not need solvents,Catalysts are m2:[Zn], amount is: 0.0 MOLE.Products are 0:FC(CC(=O)O)=C(F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: In the second method the synthesis of 4-bromo-3-chloro-3,4,4-trifluoro-butanoic acid (VIII) is followed by zinc dehalogenation to produce 3,4,4-trifluoro-3-butenoic acid (IV). This compound is prepared by reacting 1-chloro-1,2-dibromotrifluoroethane (VI) with ethyl vinyl ether in the presence of sodium dithionite and sodium bicarbonate in a manner analogous to that described in the literature [Huiang, Weiyuan; Lu, Long, Zhang, Yuanfa; Chin J. Chem. 1990, (3), 281]. However, it is now found that the 4bromo3-chloro-3,4,4-trifluorobutanal intermediate (VII) is oxidized without isolation with sodium chlorite/hydrogen peroxide. In other words, instead of oxidation with Jones reagent, this method advantageously provides a process which can be carried out in one reaction vessel using preferred reagents and gives an unexpectedly high yield |
Here is a chemical reaction formula: Reactants are m2_m3_m4_m5_m6_m8:ClC(C(Cl)(F)F)(Cl)F, amount is: 0.0 ;m2_m3_m4_m5_m6_m8:C(=C)(Cl)Cl, amount is: 0.0 ;m2_m3_m4_m5_m6_m8:S(=O)(=O)([O-])OOS(=O)(=O)[O-].[NH4+].[NH4+], amount is: 0.0 ;m2_m3_m4_m5_m6_m8:C(=O)[O-].[Na+], amount is: 0.0 ;m2_m3_m4_m5_m6_m8:O, amount is: 0.0 ;m7:C(=O)=O.CC(=O)C, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m2_m3_m4_m5_m6_m8:CN(C)C=O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC(CC(=O)O)(C(F)(F)Cl)F;0:FC(CC(=O)O)=C(F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 1,1,2-trichlorotrifluoroethane (X) (9.37 g, 50 mmol), vinylidene chloride (4.85 g, 50 mmol), ammonium persulfate (11.41 g, 50 mmol), sodium formate (3.4 g, 50 mmol) and water (1.8 g, 0.1 mol) in DMF (80 mL) was stirred (dry-ice/acetone condensor) at room temperature with air bubbling. After 30 min, an aliquot of the reaction mixture was acidified with dilute HCl, extracted with ether and analyzed by GC, which indicated the formation of two products. These products were identified by GC/MS (EI) as 4-chloro-3,4,4-trifluoro-2-butenoic acid and novel compound 3,4-dichloro-3,4,4-trifluorobutanoic acid (XI). The compound XI gives 3,4,4-trifuoro-3-butenoic acid (IV) upon reaction with zinc. Under the above reaction conditions, 1-chloro-1,2dibromotrifluoroethane (VI) gave 3-chloro-4-bromo-3,4,4-trifluorobutanoic acid (VIII) as one of the products. |
Here is a chemical reaction formula: Reactants are m1_m2_m4:BrC(C(CCBr)(F)Cl)(F)F, amount is: 0.0 ;m1_m2_m4:CN1C(CCC1)=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m4:O, amount is: 0.0 ;m3:O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:BrC(C(CCO)(F)Cl)(F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 1,4-dibromo-2-chloro-1,1,2-trifluorobutane (XVI) (7.5 g, 24.6 mmol), 1-methyl-2-pyrrolidinone (14 mL) and water (2.5 mL) was heated at 130° C. for 16 hours. The mixture was cooled to room temperature, diluted with water (80 mL) and extracted with ether (2×75 mL). The ether extract was washed with water ( 3×40 mL), brine, and dried over anhydrous magnesium sulfate. The residue obtained after evaporation of the solvent was chromatographed over silica gel to give 2.9 g (49%) of the desired alcohol as a clear oil. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:FC(CC(=O)O)=C(F)F, amount is: 0.0 ;m1_m2_m3:C(C(=O)Cl)(=O)Cl, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,Catalysts are m1_m2_m3:CN(C)C=O, amount is: 0.0 MOLE.Products are 0:FC(CC(=O)Cl)=C(F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 3,4,4-trifluoro-3-butenoic acid (IV) (19.28 g, 138 mmol), oxalyl chloride (21.8 g, 172 mmol; 15 mL) and two drops of DMF was stirred for 6 hours and distilled at atmospheric pressure under nitrogen. The fraction boiling at 90°-98° C. was collected to give 16.1 g (74%) of the desired product as a clear liquid. |
Here is a chemical reaction formula: Reactants are m1_m3_m2:N1N=CN=C1, amount is: 0.0 ;m1_m3_m2:FC(CC(=O)Cl)=C(F)F, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2:C(C)(=O)OCC, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:FC(CC(=O)N1N=CN=C1)=C(F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 1,2,4-triazole (1.38 g, 20 mmol) in ethyl acetate (100 mL) was added 3,4,4-trifluoro-3-butenoyl chloride (1.59 g, 10 mmol) at r.t. with stirring. The mixture was stirred for 30 min and filtered. The residue obtained after evaporation of the solvent was redissolved in dichloromethane (25 mL) and filtered. Evaporation of the solvent gave 1.8 g (94%) of the desired product as a clear oil. |
Here is a chemical reaction formula: Reactants are m1_m2:FC(CC(=O)NC1=CC=CC=C1)=C(F)F, amount is: 0.0 ;m1_m2:P12(=S)SP3(=S)SP(=S)(S1)SP(=S)(S2)S3, amount is: 0.0 ,this reaction does not need reagents,Solvents are m3:C1CCOC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:FC(CC(NC1=CC=CC=C1)=S)=C(F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 3,4,4-trifluoro-N-phenyl-3-butenamide (1.0 g, 4.65 mmol) and phosphorus pentasulfide (2.07 g, 4.65 mmol) in anhyd. THF (100 mL) was heated at reflux under nitrogen for 1 hour. The reaction mixture was cooled to r.t. and filtered. The filtrate was concentrated and the residue was chromatographed over silica gel (dichloromethane/hexanes, 80/20) to give 0.65 g (60%) of the desired compound as a pale yellow solid. m.p. 65°-67° C. |
Here is a chemical reaction formula: Reactants are m2_m3_m4:FC(CBr)=C(F)F, amount is: 0.0 ;m2_m3_m4:P(OCC)(OCC)OCC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m2_m3_m4:C(C)#N, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:FC(C(=C)F)(F)P(OCC)(OCC)=O;0:FC(CP(OCC)(OCC)=O)=C(F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 2,3,3-trifluoro-2-propenyl bromide (5.25 g, 30 mmol) and triethyl phosphite (4.15 g, 25 mmol) in acetonitrile (15 mL) was heated at reflux for overnight. The residue obtained after evaporation of the solvent was chromatographed over silica gel (hexanes/ethyl acetate/ethanol, 80/20/1) to give diethyl (1,1,2-trifluro-2-propenyl)phosphonate (0.8 g, 11%) and diethyl (2,3,3-trifluro-2-propenyl)phosphonate (1.0 g, 14%). |
Here is a chemical reaction formula: Reactants are m1_m3:FC(CP(OC(C)(C)C)(OC(C)(C)C)=O)=C(F)F, amount is: 0.0 ;m2:Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3:CO, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:FC(CP(O)(O)=O)=C(F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The above di-t-butylphosphonate (0.5 g) was dissolved in 3mL of methanol and treated with 0.5 mL of 3N HCl and allowed to stand at r.t. for 30 min. The solution was concentrated and the residue was redissolved in 10 mL of water and washed with 10 mL of ether. Evaporation of the aqueous layer gave 0.14 g of 2,3,3-trifluoro-2-propenylphosphonic acid as a yellow oil. |
Here is a chemical reaction formula: Reactants are m1_m6:[Mg], amount is: 0.0 ;m5_m11:C[Si](Cl)(C)C, amount is: 0.0 ;m4:[Cl-].[NH4+], amount is: 0.0 MOLE;m2_m7:BrC1=CC(=CC=C1)OC, amount is: 0.0 ;m3_m8:CN(CC(C(CC)=O)C)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m6:O1CCCC1, amount is: 0.0 ;m10:CC(CC)=O, amount is: 0.0 ;m9:CCOCC, amount is: 0.0 ;m5_m11:O, amount is: 0.0 ;m2_m7:O1CCCC1, amount is: 0.0 ;m3_m8:O1CCCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:Cl.CN(CC(C(CC)(O)C1=CC(=CC=C1)OC)C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 27.0 g (1.11 mole) of magnesium turnings were stirred in 150 ml tetrahydrofuran and 207.6 g (1.11 mole) 1-bromo-3-methoxy-benzene, dissolved in 400 ml tetrahydrofuran, were added drop-wise. The mixture was heated for one hour under reflux and was subsequently cooled to a temperature between 5° C. and 10° C. 128.30 g (0.89 mole) (RS)-1-dimethylamino-2-methyl-pentan-3-one, dissolved in 400 ml tetrahydrofuran, were added drop-wise at this temperature. The reaction mixture was allowed to stand and was subsequently cooled again to a temperature between 5° C. and 10° C. After adding 300 ml of 20 weight % ammonium chloride solution, the mixture was diluted with 400 ml ether. After phase separation the batch was extracted twice with ether, dried over sodium sulphate and the solvent was removed by distillation. The residue obtained was taken up in 3.2 l 2-butanone and treated with 120.60 g (1.11 mole) trimethylchlorosilane and 20 ml water. 121.5 g of hydrochloride (2) (38% theoretical) with a melting point of 198°-199° C. were obtained. 2nd step: |
Here is a chemical reaction formula: Reactants are m1_m2:Cl.CN(CC(C(CC)(O)C1=CC(=CC=C1)OC)C)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2:Cl, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:Cl.COC=1C=C(C=CC1)\C(\C(CN(C)C)C)=C/C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 200 g (0.69 mole) of hydrochloride (2) were dissolved in one litre of concentrated hydrochloric acid and allowed to stand at room temperature. The hydrochloric acid was removed by distillation under vacuum. The residue was dissolved in 1 l of ice-water and the pH was adjusted to 13 with 10 molar sodium hydroxide solution. After extraction with ether, drying the organic phase and removing the solvent by distillation, 162 g of crude product were obtained, and were purified by recrystallisation. 79 g (42% theoretical) of hydrochloride (1) with a melting point of 169°-170° C. were obtained. |
Here is a chemical reaction formula: Reactants are m2:Cl.COC=1C=C(C=CC1)\C(\C(CN(C)C)C)=C\CC, amount is: 0.0 MOLE;m1:ClCCl.[OH-].[Na+], amount is: 0.0 MOLE,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:Cl.CN(CC(C)/C(=C\CC)/C=1C=C(C=CC1)O)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The base was released with dichloromethane/sodium hydroxide solution from (14), which was prepared as in Example 13, and after drying the solution the dichloromethane was removed by distillation. Hydrochloride (17) was obtained, under the conditions given in Example 2, from the base thus obtained, in a yield of 86% theoretical and with a melting point of 214° C. |
Here is a chemical reaction formula: Reactants are m2:Cl.COC=1C=C(C=CC1)\C(\C(CN(C)C)C)=C/CC, amount is: 0.0 MOLE;m1:ClCCl.[OH-].[Na+], amount is: 0.0 MOLE,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:Cl.CN(CC(C)/C(=C/CC)/C=1C=C(C=CC1)O)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The base was released with dichloromethane/sodium hydroxide solution from (15), which was prepared as in Example 13, and after drying the solution the dichloromethane was removed by distillation. Hydrochloride (18) was obtained, under the conditions given in Example 2, from the base thus obtained, in a yield of 86% theoretical and with a melting point of 120°-121° C. |
Here is a chemical reaction formula: Reactants are m1_m2:Cl.CN(CC(C(C(C)C)(O)C1=CC(=CC=C1)OC)C)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2:C(=O)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:COC=1C=C(C=CC1)C(C(CN(C)C)C)=C(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Starting from (RS)-1-dimethylamino-2,4-dimethyl-pentan-3-one and 1-bromo-3-methoxy-benzene, (2RS,3RS)-1-dimethylamino-3-(3-methoxy-phenyl)-2,4-dimethyl-pentan-3-ol hydrochloride (26) was obtained, under the conditions given in Example 1 (1st step), in a yield of 44% and with a melting point of 180°-181° C. 30 g (0.1 mole) of compound (26) were reacted with 450 ml of concentrated formic acid as in Example 5. The crude base obtained was introduced on to a column packed with silica gel. Elution with 7:1 diisopropyl ether/methanol gave 19 g base (77% theoretical) as a light yellow, viscous oil. |
Here is a chemical reaction formula: Reactants are m2_m3:OCCC=O, amount is: 0.0 MOLE;m2_m3:OCCC=O, amount is: 0.0 MOLE;m5:OCCC=O, amount is: 0.0 MOLE;m6:[H][H], amount is: 0.0 MOLE;m4:OCCC=O, amount is: 0.0 MOLE,this reaction does not need reagents,this reaction does not need solvents,Catalysts are m7:[Ni], amount is: 0.0 MOLE.Products are 0:C(CCO)O;0:OCCC=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: There is produced a solution containing 8.1 percent by weight of 3-hydroxypropanal and 1.3 percent by weight of dimerized 3-hydroxypropanal both obtained as the result of the above hydration reaction. A known raney nickel catalyst is added to the resulting solution to hydrogenate 3-hydroxypropanal and dimerized 3-hydroxypropanal. Reaction conditions are: a hydrogen pressure of 100 kg/cm2, a reaction temperature of 60° C., and reaction time of six hours. When the reaction ends, the resulting solution is analyzed and it is acknowledged that there is produced 1,3-propanediol in an amount equal to a total of 3-hydroxypropanal and dimerized 3-hydroxypropanal. In other words, 1,3-propanediol is quantitatively produced. This indicates that dimerized 3-hydroxypropanal is converted into 1,3-propanediol by a known hydrogenation process. |
Here is a chemical reaction formula: Reactants are m3:COCC(=O)OC1(C(C2=CC=C(C=C2CC1)F)C(C)C)CCN(C)CCCC1=NC2=C(N1)C=CC=C2, amount is: 0.0 MOLE;m4:FC=1C=C2CCC(C(C2=CC1)C(C)C)(O)CC(=O)O, amount is: 0.0 MOLE,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:FC=1C=C2CCC(C(C2=CC1)C(C)C)(O)CC(=O)O;0:N1C(=NC2=C1C=CC=C2)CCCNC;0:N1C(=NC2=C1C=CC=C2)CCCN(C(CC2(C(C1=CC=C(C=C1CC2)F)C(C)C)O)=O)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A method of preparing 2-[2-{[3-(1H-benzimidazol-2-yl)propyl]methylamino}ethyl]-6-fluoro-1-isopropyl-1,2,3,4-tetrahydronaphthalen-2-yl methoxyacetate comprises contacting (6-fluoro-2-hydroxy-1-isopropyl-1,2,3,4-tetrahydronaphthalen-2-yl)acetic acid or an activated derivative of (6-fluoro-2-hydroxy-1-isopropyl-1,2,3,4-tetrahydronaphthalen-2-yl)acetic acid with [3-(1H-benzimidazol-2-yl)propyl]methylamine to form N-[3-(1H-benzimidazol-2-yl) propyl]-2-(6-fluoro-2-hydroxy-1-isopropyl-1,2,3 ,4-tetrahydronaphthalen-2-yl)-N-methylacetamide, reducing this to 2-[2-{[3-(1H-benzimidazol-2-yl)propyl]methylamino}ethyl]-6-fluoro-1-isopropyl-1, 2,3,4-tetrahydronaphthalen-2-ol, and treating the 2-[2-{[3-(1H-benzimidazol-2-yl) propyl]-methylamino}ethyl]-6-fluoro-1-isopropyl-1,2,3,4-tetrahydronaphthalen-2-ol with methoxyacetic acid or an activated derivative of methoxyacetic acid. The invention is particularly applicable to the preparation of mibefradil, (1S,2S)-2-[2-{[3-(1H-benzimidazol-2-yl)propyl]methylamino}-ethyl]-6-fluoro-1-isopropyl-1,2,3,4-tetrahydronaphthalen-2-yl methoxyacetate, and its dihydrochloride salt. N-[3-(1H-benzimidazol-2yl)propyl]-2-(6-fluoro-2-hydroxy-1-isopropyl-1, 2,3,4-tetrahydronaphthalen-2-yl)-N-methylacetamide is new. |
Here is a chemical reaction formula: Reactants are m2:CC(C)[C@H]1C=2C=CC(=CC2CC[C@@]1(CCN(C)CCCC=3NC=4C=CC=CC4N3)OC(=O)COC)F, amount is: 0.0 MOLE;m6:CC(C)[C@H]1C=2C=CC(=CC2CC[C@@]1(CCN(C)CCCC=3NC=4C=CC=CC4N3)OC(=O)COC)F, amount is: 0.0 MOLE;m1:[Ca], amount is: 0.0 MOLE;m5:CC(C)[C@H]1C=2C=CC(=CC2CC[C@@]1(CCN(C)CCCC=3NC=4C=CC=CC4N3)OC(=O)COC)F.Cl.Cl, amount is: 0.0 MOLE;m3:COCC(=O)O[C@]1([C@H](C2=CC=C(C=C2CC1)F)C(C)C)CCN(C)CCCC1=NC2=C(N1)C=CC=C2, amount is: 0.0 MOLE;m4:C1(=C(C(=C(C(=C1F)F)F)N)F)N.Cl.Cl, amount is: 0.0 MOLE;m7_m8_m9:FC=1C=C2CC[C@]([C@H](C2=CC1)C(C)C)(O)CCOS(=O)(=O)C1=CC=C(C=C1)C, amount is: 0.0 MOLE;m7_m8_m9:N1C(=NC2=C1C=CC=C2)CCCNC, amount is: 0.0 MOLE;m7_m8_m9:CCN(C(C)C)C(C)C, amount is: 0.0 MOLE,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:N1C(=NC2=C1C=CC=C2)CCCN(CC[C@@]2([C@H](C1=CC=C(C=C1CC2)F)C(C)C)O)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: U.S. Pat. No. 4,808,605 (to Hoffmann-La Roche) discloses various calcium antagonists including mibefradil, (1S,2S)-2-[2-{[3-(1H-benzimidazol-2-yl)propyl]methylamino}ethyl]-6-fluoro-1-isopropyl-1,2,3,4-tetrahydronaphthalen-2-yl methoxyacetate, the dihydrochloride salt of which is the antihypertensive POSICOR®. The synthesis of mibefradil, as described in that patent, involves the reaction of (1S,2S)-6-fluoro-1-isopropyl-2-[2-(4-toluenesulfonyloxy)ethyl]-1, 2,3,4-tetrahydronaphthalene-2-ol with [3-(1H-benzimidazol-2-yl)propyl]methylamine in the presence of Hunig base (ethyldiisopropylamine) to form (1S,2S)-2-[2-{[3-(1H-benzimidazol-2-yl)-propyl]methylamino}ethyl]-6-fluoro-1-isopropyl-1,2,3,4-tetrahydronaphthalen-2-ol, which is then acylated with methoxyacetyl chloride to form mibefradil. |
Here is a chemical reaction formula: Reactants are m2:FC=1C=C2CCC([C@H](C2=CC1)C(C)C)=O, amount is: 0.0 MOLE;m4:[Mg], amount is: 0.0 MOLE;m1:FC=1C=C2CC[C@]([C@H](C2=CC1)C(C)C)(O)CCOS(=O)(=O)C1=CC=C(C=C1)C, amount is: 0.0 MOLE;m3:BrCC(=O)OC(C)(C)C, amount is: 0.0 MOLE,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:FC=1C=C2CC[C@]([C@H](C2=CC1)C(C)C)(O)CC(=O)OC(C)(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The (1S,2S)-6-fluoro-1-isopropyl-2-[2-(4-toluenesulfonyloxy) ethyl]-1,2,3,4-tetrahydro-naphthalene-2-ol, as described in U.S. Pat. No. 4,680,310 (also to Hoffmann-La Roche), is prepared by reacting (S)-6-fluoro-1-isopropyl-3,4-dihydro-1H-naphthalen-2-one with tert-butyl bromoacetate in the presence of activated magnesium to form tert-butyl (1S, 2S)-(6-fluoro-2-hydroxy-1-isopropyl-1,2,3,4-tetrahydronaphthalen-2-yl)acetate, which is reduced with lithium aluminum hydride to form (1S,2S)-6-fluoro-2-(2-hydroxyethyl)-1-isopropyl-1,2,3,4-tetrahydro-naphthalen-2-ol, and then reacted with 4-toluenesulfonyl chloride in pyridine to form the (1S,2S)-6-fluoro-1-isopropyl-2-[2-(4-toluenesulfonyloxy) ethyl]-1,2,3,4-tetrahydronaphthalene-2-ol. |
Here is a chemical reaction formula: Reactants are m2:N1C(=NC2=C1C=CC=C2)CCCNC, amount is: 0.0 MOLE;m1:FC=1C=C2CCC(C(C2=CC1)C(C)C)(O)CC(=O)O, amount is: 0.0 MOLE,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:N1C(=NC2=C1C=CC=C2)CCCN(C(C[C@@]2([C@H](C1=CC=C(C=C1CC2)F)C(C)C)O)=O)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: An "activated derivative" of (6-fluoro-2-hydroxy-1-isopropyl-1,2,3,4-tetrahydro-naphthalen-2-yl) acetic acid is a derivative that renders the acid more active in the reaction with [3-(1H-benzimidazol-2-yl)propyl]methylamine to form (1S,2S)-N-[3-(1H-benzimidazol-2-yl) propyl]-2-(6-fluoro-2-hydroxy-1-isopropyl-1,2,3,4-tetrahydronaphthalen-2-yl)-N-methylacetamide. Typical such derivatives include the corresponding acyl halides and anhydrides, and a preferred activated derivative is the mixed anhydride of(6-fluoro-2-hydroxy-1-isopropyl-1, 2,3,4-tetrahydronaphthalen-2-yl)acetic acid with trimethylacetic acid. |
Here is a chemical reaction formula: Reactants are m1_m2:FC=1C=C2CC[C@]([C@H](C2=CC1)C(C)C)(O)CC(=O)OC(C)(C)C, amount is: 0.0 ;m1_m2:C(=O)O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m3:O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:FC=1C=C2CC[C@]([C@H](C2=CC1)C(C)C)(O)CC(=O)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 3.02 g crude tert-butyl (1S,2S)-(6-fluoro-2-hydroxy-1-isopropyl-1, 2,3,4-tetrahydronaphthalen-2-yl)acetate and 8 mL 96% formic acid was stirred at 25° C. for four hours. The solution was diluted with 6 mL water; then heated to 75° C and filtered. The filtrate was slowly cooled to 25° C. with stirring. The resulting suspension was cooled to 0° C., stirred for one hour, and suction filtered. The precipitate was washed with 15 mL water, air dried at 25° C. for one hour, then oven dried at 50° C. for 22 hours to give 1.59 g (1S,2S)-(6-fluoro-2-hydroxy-l-isopropyl-1, 2,3,4-tetrahydronaphthalen-2-yl)acetic acid as a colorless solid, m.p. 102-103.5° C., [α]D27 = 78.80° (CHCl3). |
Here is a chemical reaction formula: Reactants are m3:[H][H], amount is: 0.0 MOLE;m1_m4_m5_m2:C(C1=CC=CC=C1)OC1=C(C=CC=C1)C(/C=C/C1=CC=C(C(=O)[O-])C=C1)=C=O, amount is: 0.0 ;m1_m4_m5_m2:FC(C(=O)O)(F)F, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4_m5_m2:C(C)(=O)O, amount is: 0.0 MOLE,Catalysts are m1_m4_m5_m2:[Pd].[C], amount is: 0.0 .Products are 0:OC1=C(C=CC=C1)CCCC1=CC=C(C(=O)OC)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 4-[3-(2-benzyloxyphenyl)-3-carbonyl-1(E)-propenyl]benzoate (35 g), 10% Pd-carbon (7 g), acetic acid (350 mil) and trifluoroacetic acid (7 ml) was warmed at 30° C. under 10 atm. of hydrogen for 18 hours, filtered and the filtrates evaporated. The residue was triturated with hexane and dried to give methyl 4-(3-(2-hydroxyphenyl)propyl]benzoate (26 g). |
Here is a chemical reaction formula: Reactants are m1_m2_m4:[N+](=O)([O-])C=1C=C(C=CC1)COC1=C(C=CC=C1)CCCC1=CC=C(C(=O)OC)C=C1, amount is: 0.0 ;m1_m2_m4:O.O.[Sn](Cl)Cl, amount is: 0.0 ;m1_m2_m4:C(C)O, amount is: 0.0 ;m3:C([O-])(O)=O.[Na+], amount is: 0.0 MOLE,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:CC(=O)NC=1C=C(C=CC1)COC1=C(C=CC=C1)CCCC1=CC=C(C(=O)OC)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of methyl 4-[3-(2-(3-nitrophenylmethyloxy)-phenyl)propyl]benzoate (0.25 g), tin (II) chloride dihydrate (0.7 g) in ethanol (10 ml) was heated at 70° C. for 45 minutes, cooled and poured onto ice. The pH of the solution was adjusted to 8 with sodium bicarbonate and extracted with ethyl acetate (2×50 ml). The combined organics were washed with brine (50 ml), dried (magnesium sulphate), filtered and evaporated. The residue was purified by subjecting to chromatography on silica gel using ethyl acetate hexane (1:9) as eluant. There was thus obtained methyl 4-[3-(2-(3-aminophenylmethyloxy)phenyl)propyl]benzoate (185 mg). b: - Methyl 4-[3-(2-(3-methylcarbonylaminophenylmethyloxy)-phenyl) propyl]benzoate was prepared from methyl 4-[3-(2-(3-amino-phenylmethyloxy)phenyl)propyl]benzoate (preparation described in note a) as follows: |
Here is a chemical reaction formula: Reactants are m2_m3_m4:OC=1C=C(C=O)C=CC1, amount is: 0.0 ;m2_m3_m4:C(C=C)Br, amount is: 0.0 ;m2_m3_m4:C([O-])([O-])=O.[K+].[K+], amount is: 0.0 ;m1:C(C=C)OC=1C=C(CCl)C=CC1, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m5:O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C=C)OC1=C(C=O)C=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: c:- (A) 3-Allyloxybenzyl chloride was obtained as follows: A mixture of 3-hydroxybenzaldehyde (6 g), allyl bromide (6.25 g), and potassium carbonate (8.82 g) in DENT (30 ml) was stirred for 18 hours, poured into water (100 ml) and extracted with diethyl ether (3×150 ml). The combined organic extracts were washed with water (2×150 ml) and brine (2×150 ml), dried (magnesium sulphate) filtered and evaporated to give 2-allyloxybenzaldehyde (7.2 g). |
Here is a chemical reaction formula: Reactants are m1_m3_m2:C(C=C)OC=1C=C(C=O)C=CC1, amount is: 0.0 ;m1_m3_m2:[BH4-].[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2:CO, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C=C)OC=1C=C(CO)C=CC1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 3-allyloxybenzaldehyde (7.2 g) in methanol (50 ml) at 0° C. was added sodium borohydride (1 g) in portions. The mixture was stirred for 30 minutes, evaporated dissolved in 5% acetic acid and extracted with diethyl ether (3×100 ml) , washed with water (2×100 ml), and sodium bicarbonate (2×100 ml), dried (magnesium sulphate), filtered and evaporated to give 3-allyloxybenzyl alcohol (7.26 g). |
Here is a chemical reaction formula: Reactants are m3:CN(C)C=O, amount is: 0.0 MOLE;m1_m5_m2_m6:C(C=C)OC=1C=C(CO)C=CC1, amount is: 0.0 ;m1_m5_m2_m6:S(=O)(Cl)Cl, amount is: 0.0 ;m4:C([O-])(O)=O.[Na+], amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m5_m2_m6:ClCCl, amount is: 0.0 ;m1_m5_m2_m6:ClCCl, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:C(C=C)OC=1C=C(CCl)C=CC1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 3-allyloxybenzyl alcohol (7.2 g) in dichloromethane (100 ml) at 0° C. was added thionyl chloride (4.8 ml) in dichloromethane dropwise and a drop of DMF and the mixture stirred at ambient temperature for 1.5 hours, and poured into cold sodium bicarbonate solution. The organic layer was washed with sodium bicarbonate (2×100 ml), dried (magnesium sulphate), filtered and evaporated to give 3-allyloxybenzyl chloride (8.3 g). |
Here is a chemical reaction formula: Reactants are m3_m4:OC1=C(C=CC=C1)CCCC1=CC=C(C(=O)OC)C=C1, amount is: 0.0 ;m2_m5:[N+](=O)(O)[O-], amount is: 0.0 ,this reaction does not need reagents,Solvents are m3_m4:C(C)(=O)OC(C)=O, amount is: 0.0 ;m2_m5:C(C)(=O)OC(C)=O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:OC1=C(C=CC=C1[N+](=O)[O-])CCCC1=CC=C(C(=O)OC)C=C1;0:OC1=C(C=C(C=C1)[N+](=O)[O-])CCCC1=CC=C(C(=O)OC)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Nitric acid (15M, 3.13 ml) was added to acetic anhydride 12.52 ml) at 0° C. and the mixture stirred for 15 minutes, then added to a stirred solution of methyl 4-[3-(2-hydroxyphenyl)-propyl]benzoate (12.89 g) in acetic anhydride (300 ml) at 0° C. and stirred for 18 hours. The solvent was evaporated and the resulting yellow oil purified by chromatography on silica gel using ethyl acetate: hexane (1:9 to 1:1 gradient) as eluant to give methyl 4-[3-(2-hydroxy-3-nitrophenyl)propyl]benzoate (5.4 g) and methyl 4-[3-(2-hydroxy-5-nitrophenyl)propyl]benzoate (7.5 g). |